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Dissertations / Theses on the topic 'Synthesis of cyclopropanes'

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Published: 4 June 2021

Last updated: 14 February 2022

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1

Ambler, P. W. "Asymmetric synthesis of cyclopropanes." Thesis, University of Oxford, 1988. https://ora.ox.ac.uk/objects/uuid:958e77c2-d15e-4d8f-af84-36dca36e4215.

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This thesis is concerned with the asymmetric synthesis of cyclopropyl derivatives via the use of chiral iron acyl complexes of the type (η⁵-C₅H₅)Fe(CO)(PPh₃)(COCH=CR'R), Chapter 1 reviews previous routes to optically active cyclopropyl derivatives and reviews the use of the chiral auxiliary (η⁵-C₅H₅)Fe(CO)(PPh₃) for asymmetric synthesis. Chapter 2 describes the synthesis of the complexes (η⁵-C₅H₅)Fe(CO)(PPh₃)(COCH=CRR') and presents a conformational analysis of the α, β-unsaturated acyl ligand. Chapter 3 describes the diastereoselective synthesis of cis- substituted cyclopropyl complexes via the reaction of Z-α, β-unsaturated iron acyl complexes with electrophilic alkylidene species. Decomplexation, to give the corresponding cyclopropyl esters, occurred without epimerisation of the cyclopropane ring. By the use of homochiral iron acyl complexes the enantioselective synthesis of cyclopropyl derivatives was achieved. Section A describes methylene addition and Section B isopropylidene addition reactions. Section C describes attempts to synthesise pyrethroid insecticide precursors which occurred with good diastereoselectivity but poor regioselectivity. Section D describes electrophilic ethylidene addition reactions in which the chiral auxiliary exerts good stereochemical control over three new chiral centres. Chapter 4 describes the diastereoselective synthesis of trans- substituted cyclopropyl complexes via the reaction of E-α, β-unsaturated iron acyl complexes with nucleophilic alkylidene transfer reagents. Section A describes methylene transfer reagents. Whilst α-lithiosulphides and α-lithiosulphoxides were of limited use, iodomethyllithium (generated in situ) resulted in highly diastereoselective syntheses of the cyclopropyl complexes. Decomplexation, to give the corresponding cyclopropyl esters, occurred without epimerisation of the cyclopropane ring. By the use of homochiral iron acyl complexes the enantioselective synthesis of cyclopropyl derivatives was achieved. Section B describes the generation of 1-iodoethyllithium and 1-iodobutyllithium and their reactions as nucleophilic alkylidene transfer reagents. The stereo- chemistry at two of the new chiral centres is controlled by the iron chiral auxiliary, whilst that at a third is controlled by a number of factors.

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2

Watson, Hayley. "Synthesis and reactivity of cyclopropanes and cyclopropenes." Thesis, Loughborough University, 2011. https://dspace.lboro.ac.uk/2134/9032.

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Activated cyclopropanes have been extensively used in synthetic chemistry as precursors for cycloaddition reactions. The rationale behind this is their ability to undergo ring-opening when activated by a Lewis acid, this can be enhanced further by the presence of a carbocation stabilising group like electron-rich aromatics. The stabilised dipole formed after ring opening can be trapped with suitable electrophiles such as imines and aldehydes via a [3+2] cycloaddition reaction. This results in the synthesis of pyrrolidines and tetrahydrofurans in excellent yields but moderate diastereoselectivity. Similarly, 6-membered heterocycles can be formed via a [3+3] cycloaddition reaction of activated cyclopropanes with nitrones. Now to extend the scope of the methodology, a [3+3] dipolar cycloaddition has been developed using activated 2,3 disubstituted cyclopropane diesters to access a range of highly functionalised oxazines in moderate to good yields (50-75%) and with reasonable diastereoselectivity. The use of activated symmetrical disubstituted cyclopropanes afforded the desired oxazines in a regio- and diastereocontrolled manner, while the use of unsymmetrical cyclopropanes significantly reduced the diastereoselectivity of the reaction. The stereochemistry outcome of the reaction developed was determined by nOe analyses and X-ray diffraction structures could be recorded in some examples. A new methodology has also been developed to gain access to novel N-heterocyclic- and phenol- substituted cyclopropanes in one step from the corresponding cyclopropene via a conjugated addition.

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3

Minicone, Fabrizio. "Stereoselective synthesis of cyclopropanes with quaternary carbon centres." Thesis, Queen Mary, University of London, 2014. http://qmro.qmul.ac.uk/xmlui/handle/123456789/8766.

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Multi-substituted optically pure cyclopropanes are important motifs present in many agrochemicals, pharmaceuticals and materials employed in manifold applications. Their synthesis is challenging due to both the strained conformation and the need to control both the relative and absolute stereochemistry. This thesis describes an investigation of the scope of the Wadsworth-Emmons cyclopropanation, highlighting it as a potential efficient methodology for diastereoselective and enantiospecific synthesis of these valuable ring systems. Chapter 1 is an introduction to the cyclopropanation protocols and is split in two subsections. The first is a description of the currently most exploited synthetic pathways to cyclopropanes, with analysis of their substrate scope and critical analysis of their limitations as compared to potential of the Wadsworth-Emmons cyclopropanation (Sections 1.1 to 1.3). The latter section consists of a review on the history and the evolution of this procedure and introduces the preconditions for the development of the project (Sections 1.4 to 1.17). Chapter 2 describes the results and discussion, introducing the use of novel alkyl-substituted triethyl phosphonoacetates to yield cyclopropyl-esters containing quaternary stereocentres. The high yields and the excellent trans-diastereoselectivity values obtained (proved by X-ray crystallography) allowed the proposal of a suggested reaction mechanism, which is supported by the subsequent experiments carried out in the presence of other functional groups, e.g. other carbonyls, nitriles, hetero-aromatics, substituted phenyl rings. This study was further extended to examine the effect of fluorine atom, due to its importance in biologically active environments. The study on the stereochemistry of the Wadsworth-Emmons cyclopropanation has been strongly supported by a range of X-ray crystal structures of the cyclopropane products. The chapter ends with an empirical set of guidelines, helpful for the design of successful cyclopropanations. Chapter 3, describes the experimental methods in full as well as full characterisation of the products obtained. Literature references, noted throughout the thesis, are listed in the final chapter.

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4

Sweesi, Miloud E. M. "Studies of the synthesis of cyclopropanes and cyclobutenes." Thesis, Bangor University, 2006. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.438828.

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5

Clarke, C. "Comparative chemistry of protected phosphines within the synthesis of cyclopropanes." Thesis, University of Cambridge, 2004. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.597723.

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On treatment with base, diphenylphosphinoyl esters 3 (X=O) give cyclopropanes 4 via a series of steps including intramolecular acyl and phosphinoyl transfer processes. β-Substituted esters have been shown to give cyclopropanes with high diastereoselectivity. This thesis describes the synthesis of optically active β-substituted esters using Evans’ alkylation methodology and their use in the stereocontrolled synthesis of substituted cyclopropanes. It was found that that phosphine oxide 1 (X=O) is unstable in the conditions of the alkylation reaction and the corresponding phosphine borane 1 (X=BH₃) was employed with greater success. The thesis also describes investigations into the potential formation of cyclopropanes 4 from esters 3 (X= BH₃/S) without prior conversion to the phosphine oxide 3 (X=O). It has been proposed that a phosphine ester is a key intermediate in the formation of cyclopropanes 4 from diphenylphosphinoyl esters 3 (X=O). Detailed in this thesis, is an investigation into the synthesis of optically active cyclopropanes 8 from phosphonate esters 7 prepared by an Evans’ alkylation route. Also included in this thesis are studies into the relative rates of deprotonation and the palladium-catalysed hydrogenation reactions of allyl phosphine oxides, boranes and sulfides. Phosphine oxides have also been used in the synthesis of cyclopropanes via a route analogous to that of the Wadsworth-Emmons cyclopropanation reaction.

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6

Ner, S. K. "The synthesis and testing of cyclopropane inhibitors of Carboxypeptidase A." Thesis, University of Strathclyde, 1986. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.381719.

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7

Huang, Weisheng. "Catalytic asymmetric cyclopropanation and oxidation of tri-, di- and monofluoromethyl styrenes Rhodium catalysed enantioselective synthesis of mono-(halo)-methyl-cyclopropanes Catalytic enantioselective synthesis of highly functionalized difluoromethylated cyclopropanes General catalytic enantioselective access to monohalomethyl and trifluoromethyl cyclopropanes Catalytic asymmetric synthesis of α,α-difluoromethylated and α-fluoromethylated tertiary alcohols." Thesis, Normandie, 2019. http://www.theses.fr/2019NORMIR25.

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Ce manuscrit décrit la synthèse énantiosélective de cyclopropanes trifluorométhylés, difluorométhylés et mono-halométhylés hautement fonctionnalisés. Cette synthèse repose sur la cyclopropanation d’alcènes. De plus, la synthèse d’alcools tertiaires difluorométhylés à partir des oléfines fluorées correspondantes suivant un processus de dihydroxylation asymétrique est décrite. Ce manuscrit se découpe en 3 chapitres. Le premier chapitre décrit la première synthèse catalytique asymétrique de cyclopropanes difluorométhylés en utilisant le Rh₂((S)-BTPCP)₄ comme catalyseur pour la réaction de cyclopropanation d’oléfines α,α-difluoromethylées avec des composés diazoïques di-accepteurs. Un large éventail de cyclopropanes a été obtenu avec de très bon rendements et d’excellentes diastéréosélectivités et énantiosélectivités (>20:1 et jusqu’à 99% ee). Le second chapitre illustre la synthèse de cyclopropanes trifluorométhylés suivant une stratégie similaire. Ces derniers ont été obtenus avec des très bons rendements et d’excellentes diastéréosélectivités et énantiosélectivités (>20:1 et jusqu’à 99% ee). Ces travaux ont également permis une extension aux dérivés mono-halométhylés. Dans un troisième chapitre, l’époxydation asymétrique de styrenes α,α-difluoromethylés a été étudiée. Malheureusement, tous les essais métallo- ou organocatalysés se sont avérés infructueux. Par la suite la réaction de dihydroxylation asymétrique de ces styrenes α,α-difluorométhylés a été développée pour conduire aux alcools tertiaires difluorométhylés énantioenrichis. L’utilisation d’AD-mix-α et AD-mix-β comme catalyseurs a permis d’obtenir les produits désirés avec de très bons rendements et d’excellentes énantiosélectivités. De plus, cette réaction a été étendue aux styrenes α,α-difluorométhylés, α-monofluorométhylés, β-difluoromethylé et β-trifluorométhylé
This thesis presents the enantioselective synthesis of functionalized trifluoromethyl, difluoromethyl and monohalomethyl cyclopropanes based on the cyclopropanation reaction of alkenes bearing various fluorinated groups. In addition, the synthesis of enantioenriched fluorinated tertiary alcohols resulting from the dihydroxylation of fluorinated olefins is discussed. This thesis is divided into three chapters. In the first chapter, we reported the first example of catalytic asymmetric synthesis of difluoromethyl cyclopropanes, which is achieved by using Rh₂((S)-BTPCP)₄ as a catalyst to perform the cyclopropanation reaction of α,α-difluoromethyl olefins with donor-acceptor diazo compounds and di-acceptor diazo compounds. This methodology allows the access to a broad range of cyclopropanes in high yields with excellent diastereo- and enantioselectivities (up to >20:1 and up to 99% ee). In the second chapter, a practical and efficient asymmetric synthesis of trifluoromethyl cyclopropane derivatives was described and a series of functionalized cyclopropanes were obtained in excellent diastereoselectivities with excellent enantioselectivities (up to >20:1 and 99% ee). These investigations also extended to the synthesis of highly enantioselective monohalomethyl cyclopropanes. In the third chapter, the initial propose aimed at exploring the asymmetric epoxidation of α,α-difluoromethyl styrenes. The reaction was performed in the presence of a metal-catalyst or an organic catalyst, unfortunately, none of the result was positive. Therefore, we turned our attention to the asymmetric synthesis of α,α difluoromethylated tertiary alcohols. To this propose, the use of commercially available reagents AD-mix-α and AD-mix-β as the best catalysts, allowed the reaction with α,α-difluoromethyl styrenes to construct the corresponding α,α-difluoromethylated tertiary alcohols in good to high yields with excellent enantioselectivities (up to 99% ee). In addition, this transformation could be applied to a broad range of substrates, including variety of α,α-difluoromethyl styrenes, α-monofluoromethyl styrenes, β-difluoromethyl styrene and β-trifluoromethyl styrene

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8

Dorsey, Gordon Owen. "Design and synthesis of substituted cyclopropanes as conformationally restrained dipeptide mimics." Thesis, Austin, Texas : University of Texas at Austin, 1992. http://handle.dtic.mil/100.2/ADA252441.

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Thesis (M.A. in Chemistry)--University of Texas at Austin, May 1992.
"May 1992." Description based on title screen as viewed on April 8, 2009. Includes bibliographical references (p. 94-101). Also available in print.

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9

Ivashkin, Pavel. "Synthesis of original fluorinated cyclopropylcarboxylates." Phd thesis, INSA de Rouen, 2013. http://tel.archives-ouvertes.fr/tel-00924650.

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Organofluorine compounds constitute a large part of all the drugs, crop protection agents and advanced materials produced nowadays. Therefore, there is a great interest in developing the new methods of synthesis of organofluorine compounds. In this thesis we report a novel method of synthesis of monofluorinated cyclopropanes based on the Michael-initiating ring closure (MIRC) reaction. Our method allows obtaining polysubstituted monofluorinated cyclopropanes from ethyl dibromofluoroacetate and various Michael acceptors. We have also implemented the asymetric version of cyclopropanation using a novel oxazolodinone-derived chiral fluorinated reagent. In the final part of this thesis we report the synthesis of a fluorinated analog of L-FAP4, a potent agonist of group II metabotropic glutamate receptors (mGluR II). Incorporation of a fluorine atom is expected to increase the biological activity and bioavailabiblity of this compound.

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10

Highton, Adrian. "Organic synthesis using iron (III) mediated fragmentation reactions of silyoxycyclopropanes." Thesis, University of Nottingham, 2000. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.311749.

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11

Pale, Patrick. "Synthese et reactivite d'epoxyalcools acetyleniques chiraux : application a la synthese de cyclopropanes et d'heterocycles fonctionnalises." Reims, 1988. http://www.theses.fr/1988REIMS012.

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12

Hackett, Siobhán. "Exploring the reactions of small rings." Thesis, Queen Mary, University of London, 2014. http://qmro.qmul.ac.uk/xmlui/handle/123456789/8965.

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Small rings are frequently found in natural products as well as incorporated into drugs and agrochemicals in which they impart valuable properties on the biological activity of these compounds. Cyclopropanes are also extremely useful as reagents in organic synthesis, in particular as “umpolung” reagents, allowing access to products which would otherwise be more difficult to synthesise. This thesis will describe forays into the synthesis and further substitution of small rings as well as the iminium-catalysed ring-opening of cyclopropanes. The introduction will outline the uses and properties of cyclopropanes, and will also describe some of the more common ways for incorporating cyclopropanes into larger structures. This will include the Horner–Wadsworth–Emmons procedure which has previously been developed by the group. The second chapter describes efforts towards the iminium-catalysed nucleophilic ring-opening of cyclopropanes. This is followed by Chapter 3, in which the Horner–Wadsworth–Emmons methodology for the synthesis of the cyclopropanes used in Chapter 2 is investigated as a procedure for the synthesis of 4-membered heterocycles. Chapter 4 describes the development of a decarboxylative method for the protodecarboxylation of cyclopropanecarboxylic acids. This was developed as the first step towards decarboxylative cross-coupling of cyclopropanes. Decarboxylative cross-couplings have been extensively developed as environmentally friendly and facile alternatives to the current cross-coupling methods. In Chapter 5 the attempted development of a decarboxylative cross-coupling reaction of cyclopropanes is described. Conclusions and future work are outlined in Chapter 6, followed by the experimental details in Chapter 7.

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13

Huber, Florian Anton Martin. "Stereocontrolled cyclopropane synthesis." Thesis, Bangor University, 1999. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.297672.

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14

Pedersen, Daniel Sejer. "Asymmetric cyclopropane synthesis." Thesis, University of Cambridge, 2006. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.613762.

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15

Patil, Dadasaheb V. "Intramolecular cyclization strategies for synthesizing medium-ring polycycles and the total synthesis of natural products." Diss., Georgia Institute of Technology, 2012. http://hdl.handle.net/1853/50118.

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Carbo- and heterocyclic compounds are of great interest to chemists. Intramolecular cyclization strategies of donor-acceptor (D-A) cyclopropanes and alkylidene malonate monoamides have excellent potential for synthesis as they offer easy access to structurally-diverse compounds. The work described in this thesis accesses the scope of the In(OTf)3-catalyzed cyclization reaction of cyclopropanes and alkylidene malonate monoamides. In(OTf)3-catalyzed reactions of alkenyl and heteroaryl cyclopropyl ketones were examined in the synthesis of functionalized cyclohexenone-based derivatives (Chapter 2). Subsequent efforts to utilize a tandem cyclopropane ring-opening/Friedel-Crafts alkylation sequence of methyl 1-(1H-indolecarbonyl)-1-cyclopropanecarboxylates to prepare functionalized hydropyrido[1,2-a]indole-6(7H)-ones is discussed in Chapter 3. The extension of this tandem protocol towards the total synthesis of (±)-deethyleburnamonine is the subject of Chapter 6. Intramolecular Friedel-Crafts alkylation of N-indolyl alkylidene malonate monoamides was also examined. An In(OTf)3-catalyzed cyclization of substituted methyl 2-(1H-indole-1-carbonyl) acrylates afforded a series of 1H-pyrrolo[1,2-a]indole-3(2H)-ones (Chapter 4), whereas substrates with the indole 2-position blocked provided access to substituted 4H-pyrrolo[3,2,1-ij]quinolin-4-ones (Chapter 5).

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16

Thomas, Stephen Patrick. "Phosphorus mediated asymmetric cyclopropane synthesis." Thesis, University of Cambridge, 2007. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.613118.

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17

Mohanathas, Rajaratnam. "Synthetic studies of cyclopropanes and cyclobutanes." Thesis, Bangor University, 2006. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.431491.

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18

Jacoby, Denis. "Synthese et reactivite des cyclopropanes actives." Paris 6, 1987. http://www.theses.fr/1987PA066439.

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Ce travail decrit des mises au point originales de preparations de pyrrolines et de dihydrofurannes a partir de cyclopropylcetoesters. Ces derniers sont prepares a partir de sels de triphenylphosphonium, precurseurs de derives cyclopropaniques. La reactivite de ces composes cyclopropaniques vis a vis de nucleophiles varies est etudiee. L'action des amines primaires permet d'obtenir des pyrrolines. Une etude biologique montre l'activite biocide des composes prepares

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19

Coxon, Geoffrey David. "The synthesis and chirality of cyclopropane fatty acids." Thesis, University of Newcastle Upon Tyne, 1999. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.285742.

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20

Licence, Peter. "Synthetic studies in cyclopropane chemistry." Thesis, Bangor University, 2000. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.364988.

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21

DIEP-VOHUULE, NGOC-ANH. "Synthese asymetrique d'epoxydes et de cyclopropanes chiraux." Université Louis Pasteur (Strasbourg) (1971-2008), 1996. http://www.theses.fr/1996STR13269.

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Le travail decrit dans ce memoire porte sur la synthese asymetrique d'epoxydes et de cyclopropanes enantiomeriquement enrichis au depart des ylures de soufre chiraux derives de (+)-(r,r,r) ou de (-)-(s,s,s)-oxathiane d'eliel 1. Nous avons mis au point une methode de synthese asymetrique courte d'epoxydes mono et disubstitues ayant une purete enantiomerique elevee de 84 a 99. 9%. Cette methode est aisement realisee en deux etapes a partir de l'oxathiane d'eliel 1: une s-alkylation stereoselective de l'oxathiane 1 par un triflate ou un halogenure d'alkyle ou d'aryle conduit au sel de sulfonium qui, en presence d'une base et d'un aldehyde conduit en milieu aprotique aux epoxydes desires avec recuperation de l'auxiliaire chiral 1. L'application de cette methode a permis la preparation de deux composes -adrenergiques de configuration (r) desiree, le (-)-(r)-dichloroisoproterenol et le (-)-(r-)-pronethalol, ainsi qu'un cristal liquide cholesterique, le (+)-(r,r)-1-(p-cyanophenyl)-2-(p-octyloxyphenyl)-epoxyde trans. Finalement, nous avons montre qu'il etait possible, par cette methode, d'acceder a des cyclopropanes disubstitues avec des exces enantiomeriques eleves de 95 a 100%. Cette methode nous offre la possibilite de preparer pour la premiere fois le (s,s)-1-carboethoxy-2-t-butylphenylcyclopropane, un intermediaire cle dans la synthese du (s)-fenpropimorph

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22

Glen, Anthony D. "Synthetic studies on cyclopropane fatty acids." Thesis, University of Newcastle Upon Tyne, 1994. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.386040.

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23

Campbell, Matthew James Johnson Jeffrey Scott. "I. Mechanistic studies of a copper-catalyzed electrophilic amination of diorganozinc reagents reagents by O-benzoyl N,N-dialkylhydroxylamines II. Development of a 3-Exo-Dig cyclization for the preparation of vinylidene cyclopropanes III. Total synthesis of +-polyanthellin A." Chapel Hill, N.C. : University of North Carolina at Chapel Hill, 2009. http://dc.lib.unc.edu/u?/etd,2881.

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Thesis (Ph. D.)--University of North Carolina at Chapel Hill, 2010.
Title from electronic title page (viewed Jun. 23, 2010). "... in partial fulfillment of the requirements for the degree of Doctor of Philosophy in the Department of Chemistry." Discipline: Chemistry; Department/School: Chemistry.

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24

Walther, Stefan. "Cyclopropane als Edukte zur Synthese von Calicenen /." [S.l : s.n.], 1985. http://www.ub.unibe.ch/content/bibliotheken_sammlungen/sondersammlungen/dissen_bestellformular/index_ger.html.

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25

Pietruszka, Jörg. "Enantiomerenreine Cyclopropane : neue Bausteine für die Natur- und Wirkstoffsynthese /." Herdecke : GCA-Verl, 2001. http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&doc_number=009621579&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA.

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26

Hanlon, David James. "u-vinylidene and n-1-cyclopropenyliron complexes : chemistry and synthesis via 1, 1-dichlorocyclopropanes /." Full-text version available from OU Domain via ProQuest Digital Dissertations, 1985.

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27

Jevric, Martyn. "Synthesis of 1,2-Dihydronaphtho[2,1-b]furans. Reactions of 1,2-Dioxines and stabilised phosphorus ylides /." Title page, Index and abstract only, 2004. http://web4.library.adelaide.edu.au/theses/09PH/09phj589.pdf.

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28

GRANDJEAN, DIDIER. "Synthese enantioselective d'epoxyde et de cyclopropanes. Application a la synthese de produits naturels." Reims, 1991. http://www.theses.fr/1991REIM5008.

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Dans ce travail, deux molecules chirales extremement importantes sur le plan synthetique ont ete preparees, l'une epoxydique: le (2s,3r)-4-butyryloxy-2,3-epoxybutan-1-ol, l'autre cyclopropanique: le (1r,2s)-1-butyryloxymethyl-2-hydroxymethylcyclopropane. Ces deux synthons, optiquement purs, ont ete obtenus par hydrolyse enzymatique des diols diesterifies meso correspondants. L'epoxyalcool(2s,3r)-4-butyryloxy-2,3-epoxybutan-1-ol a ete transforme en epoxyalcools acetyleniques cis diversement substitues. L'etude de ces ethynyloxiranes nous a permis de mettre en evidence trois nouveaux aspects de leur reactivite. Le couplage yne-yne dissymetrique selon la methode de cadiot-chodkiewicz entre des epoxydes acetyleniques bromes et des acetyleniques vrais conduit avec d'excellents rendements aux epoxydiynes correspondants. De cette maniere, deux molecules naturelles presentant des activites insecticides antiappetantes ont pu etre synthetisees: le (2z,8s,9r)-8,9-epoxy-10-hydroxydeca-2-en-4,6-diyn-1-oate de methyle et son acetate. L'heterocyclisation d'alcools acetyleniques bromes en milieu basique fournit regio et stereospecifiquement les bromoethylenetetrahydrofuranes correspondants quantitativement. Cette meme reaction appliquee aux epoxyalcools diyniques donne la meme regiospecificite mais n'est pas stereoselective. Cette nouvelle reaction de cyclisation offre des perspectives tres interessantes pour la synthese de produits naturels. La deprotonation d'ethynyloxiranes permet d'acceder a des epoxydes acetyleniques trisubstitues. Le piegeage des anions oxiranyles intermediaires par des electrophiles s'effectue avec retention de configuration et sans racemisation. Quant a l'alcool cyclopropanique (1r,2s)-1-butyryloxymethyl-2-hydroxymethyl-cyclopropane enantiomeriquement pur, celui-ci nous a permis de synthetiser deux produits naturels extraits d'algues brunes dictyopteris: le dictyopterene a et le dictyopterene c. L'acces rapide de ces dictyopterenes a ete rendu possible grace a des reactions de type wittig hautement stereoselectives. Au cours de la synthese du dictyopterene a, une epimerisation d'un des carbones du cyclopropane a ete mise au point. De ce fait, le synthon cyclopropanealcool obtenu par hydrolyse enzymatique pourrait permettre de synthetiser non seulement tous les dictyopterenes, mais aussi d'acceder a n'importe quel cyclopropane disubstitue cis ou trans optiquement pur. L'etude du rearrangement thermique du vinylethynyloxirane optiquement actif le plus simple en formylethynylcyclopropane nous a permis de montrer que cette isomerisation s'effectuait avec un transfert total de chiralite. La configuration absolue des carbones du formylethynylcyclopropane obtenu par reaction thermique a pu etre etablie en comparant le signe de son pouvoir rotatoire avec celui de la meme molecule preparee a partir du cyclopropanediol monoprotege issu de l'hydrolyse enzymatique. Ainsi, le mecanisme intime de cette isomerisation thermique a pu etre deduit

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29

Jerome, L. "The generation and reactivity of functionalised organozinc carbenoids for cyclopropane synthesis." Thesis, University College London (University of London), 2009. http://discovery.ucl.ac.uk/17481/.

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This thesis describes the generation and reactivity of functionalised organozinc carbenoids for cyclopropane synthesis with alkenes. In the introductory chapter, a brief overview of the different methods for preparation of heteroatom-functionalised cyclopropanes is presented, including [2+1] cycloaddition reactions using a carbene or carbenoid as a cyclopropanating agent with an alkene, ionic stepwise methods, and chemical modifications from existing cyclopropanes. The remainder of this chapter then focuses on previous work within our own group in this area. The second chapter presents the results obtained from different areas of research in the present study, the first of these being a deeper understanding and extension of the research work undertaken by my predecessor for the development of the cyclopropanation reaction using an “amidoorganozinc” carbenoid derived from N,N diethoxymethyloxazolidinones derivatives in the presence of a source of zinc and chlorotrimethylsilane. Thus, the chemoselectivity and stereoselectivtity of the reaction were fully studied, and a quadrant model was constructed to rationalise the stereochemistry of the products obtained. The second part of this section outlines the generation of new enantiopure organozinc carbenoids precursors derived from substituted chiral precursors followed by the synthesis of novel enantiopure highly functionalised N-cyclopropyl oxazolidinones. The intramolecular version of this cyclopropanation reaction was then successfully studied using diethoxylactam derivatives as organozinc carbenoid precursors. The methodology was then applied to the preparation of novel aminocyclopropyl functionalised compounds selected as interesting building blocks which can lead to the synthesis of natural and biologically active compounds. The fifth part of this chapter describes subsequent studies towards the design of new carbenoid precursors containing additional functional groups of interest. Finally, a brief study on the potential of an organozinc carbenoid to participate in a novel [2,3] sigmatropic rearrangement was investigated. The thesis concludes with a summary of the results obtained, a detailed description of the experimental procedures used and the characterization and analysis of the compounds prepared, together with a full bibliography.

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Troxler, Thomas. "B₁₂-katalysierte, enantioselektive Isomerisierung von Cyclopropanen : Synthese von Carbovir /." Bern, 1993. http://www.ub.unibe.ch/content/bibliotheken_sammlungen/sondersammlungen/dissen_bestellformular/index_ger.html.

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NEVELLEC, LAURENCE. "Synthese d'analogues de nucleosides cyclobutaniques et cyclopropaniques." Le Mans, 1995. http://www.theses.fr/1995LEMA1018.

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Ce travail est axe sur la synthese d'analogues de nucleosides cyclobutaniques et cyclopropaniques a visee antivirale, par differentes voies d'introduction directe de la base purique ou pyrimidique sur des carbocycles fonctionnalises. Des composes cyclobuteniques ont ete synthetises a partir de l'anhydride cis-4-cyclobut-3-ene-1,2-dicarboxylique, obtenu par la reaction photochimique entre l'acetylene et l'anhydride maleique. L'ouverture nucleophile d'epoxydes cyclobutaniques en derivant a ainsi conduit a la synthese d'analogues de nucleosides cyclobutaniques trihydroxyles. La contraction de cycle c4-c3 stereoselective d'un -bromocyclobutanol en milieu basique a permis d'acceder a un aldehyde cyclopropanique, precurseur d'un analogue de nucleoside cyclopropanique-1,2,3 trisubstitue possedant un groupe methylene entre la base et le carbocycle. Cette approche constitue une voie originale dans la synthese d'analogues de nucleosides cyclopropaniques. L'introduction directe de l'adenine s'est egalement operee par substitution nucleophile d'un mesylate cyclobutanique. Seul le mesylate de stereochimie cis a conduit a la synthese d'un analogue de nucleoside cyclobutanique dihydroxyle. Dans des conditions de reaction de couplage identiques, le mesylate de stereochimie trans, a conduit a une regression de cycle dont certains aspects mecanistiques ont ete determines par deuteriation du mesylate en deux positions. Tous ces travaux ont necessite une etude approfondie en rmn: la mesure d'effets noe a permis la determination de la stereoselectivite des reactions, notamment lors de l'addition de phsecl sur differents cyclobutenes. L'identification de la regiochimie des attaques nucleophiles de la base heterocyclique a ete effectuee grace a diverses sequences en rmn

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BERUBEN, DOV. "Carbometallation diastereoselective de vinylmetaux. Application a la synthese de cyclopropanes metalles." Paris 6, 1994. http://www.theses.fr/1994PA066050.

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Au cours de ce travail, nous avons realise la carbometallation d'ethers allyliques metalles en position 3, pour obtenir la formation d'un organogembismetallique-1,1. Dans des conditions experimentales precises, celui-ci peut subir une reaction d'elimination -1,3 pour conduire au cyclopropylmetal correspondant, via un etat de transition en w, avec double inversion de configuration au niveau des centres reactifs. Ce meme protocole a pu etre realise a partir d'ethers homoallyliques secondaires metalles en position 3. Un organogembismetallique-n,n dialkyle est alors mis en evidence pour la premiere fois. Celui-ci peut, dans des conditions analogues, conduire a un cyclopropylmetal tertiaire sous forme d'un seul isomere, presentant une relation syn entre les deux substituants. Cependant, la diastereoselectivite du processus d'elimination-1,3 peut etre modifiee si le methoxymethyl ether est soit benzylique, soit vinylique. Dans ce cas, l'intermediaire bimetalle adopte une conformation relative differente dans laquelle le metal, ne participant pas a l'elimination, se coordine au systeme insature. Cette interaction dipolaire, bien que deja decrite dans la litterature, n'a jamais eu a notre connaissance d'implication sur la stereochimie. Or, elle apparait responsable ici, de la stereochimie du cyclopropane. Toutefois, une interaction sterique-1,2 a de meme ete mise en evidence et semble etre predominante sur le deroulement stereochimique lors de l'elimination-1,3. Il a ete ainsi possible d'etablir un ordre de preseance des differents groupements qui influent sur la stereochimie

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33

盧偉祥 and Wai-cheung Lo. "Metal complexes of porphyrins and porphycenes in catalytic cyclopropanation and aziridination of alkenes." Thesis, The University of Hong Kong (Pokfulam, Hong Kong), 1998. http://hub.hku.hk/bib/B31237484.

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Chawner, Stephen John. "Divergent synthesis of cyclopropane-containing fragments and lead-like compounds for drug discovery." Thesis, Imperial College London, 2017. http://hdl.handle.net/10044/1/56635.

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The cyclopropane ring is key to a large number of medicinally‑relevant compounds that possess a broad spectrum of biological activities. This thesis details the preparation of novel bifunctional cyclopropanes through a divergent functionalisation approach utilising two readily accessible cyclopropyl‑scaffolds. The cyclopropanes generated sampled new areas of chemical space whilst being suitable 3‑dimensional fragments and lead-like compounds for drug discovery. A novel CoII-catalysed cyclopropanation generates two diastereoisomeric bifunctional cyclopropyl-scaffolds from commercially available reagents in an excellent yield and can be conducted on multi-gram scales. Asymmetric cyclopropanation has been explored with max ee = 73%. Divergent functionalisation of the ester was explored, utilising hydrolysis, reduction and amidation reactions to create a variety of functionalised cyclopropyl sulfides. The sulfide synthetic handle was oxidised to give the corresponding sulfoxides or sulfone selectively. Sulfoxide–magnesium exchange was explored and the cyclopropyl-organometallic species generated was trapped with a variety of electrophiles to create a diverse range of cyclopropane-containing products. The cyclopropyl-organometallic species was also utilised in Negishi cross-coupling, proving to be a versatile method to attach an aromatic or heteroaromatic directly onto the cyclopropane ring.

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35

Badiani, Kamal. "Synthesis and evaluation of enzyme inhibitors based on amino- and cyclopropane carboxylic acids." Thesis, University of St Andrews, 1997. http://hdl.handle.net/10023/14052.

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The coenzyme B12-dependent enzyme, glutamate mutase (E. C. 5.4.99.1), catalyses the reversible carbon-skeleton rearrangement of (2S)-glutamic acid to (25.35)-3-methylaspartic acid. Glutamate mutase is the first enzyme on the mesaconate pathway. A variety of glutamate and 3-methylaspartate analogues (which also include isotopically labelled molecules), were synthesised as molecular probes of the enzyme. Synthesis of stereospecifically labelled 3-ethylaspartic acid: (2S,3S)-[3'-C2H3], and (2S,3S)-[C2H2C2H3]-ethylaspartic acids were constructed using appropriately labelled iodoethane. (2S,3S)-2-Bromo-3-methylsuccinic acid was synthesised via the diazotization of (2S,3S)-3-methylaspartic acid, in the presence of bromide ion. (2S)-Methylsuccinic acid was synthesised by the catalytic hydrogenation of (2S,3S)-2-bromo-3-methylsucdnic acid. Biological studies of the synthesised compounds (including the labelled isotopomers) displayed no activity against glutamate mutase. 3-Methylaspartate ammonia-lyase, the second enzyme in the mesaconate pathway, catalyses the deamination of (2S,3S)-3-methylaspartic acid to mesaconic acid. A range of 1-substituted cyclopropane 1,2-dicarboxylic acids were synthesised using short efficient routes and were found to be good to potent inhibitors of 3-methylaspartase. X-ray crystallographic studies have determined the absolute stereochemistry. The mode of action of the most potent inhibitor, (1S,2S)-1-methylcyclopropane 1,2-dicarboxylic acid (20 mumol dm-3), is consistent with it acting as a transition state analogue for the central substrate deamination reaction catalysed by the enzyme. beta-Amino acids are constituents of many biologically active peptides. A general procedure for the synthesis of alpha-substituted-beta-amino acids has been developed. The synthesis involves a Baylis-Hillman amine catalysed conversion of methyl acrylate, with an appropriate aldehyde, to give the alpha-(hydroxyalkyl) acrylate. Bromination and subsequent azide displacement furnishes the azido alkene, which is catalytically hydrogenated, to furnish the beta-amino ester.

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Johnson, William T. G. "Synthesis of precursors of a highly pyramidalized alkene and ab initio calculations on methylenecyclopropane, cyclopropene, and 1,3-diradicals /." Thesis, Connect to this title online; UW restricted, 1999. http://hdl.handle.net/1773/11586.

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Natchus, Michael George. "Low-temperature vinylcyclopropane rearrangement in the total synthesis of (-) - specionin." Diss., Virginia Tech, 1992. http://hdl.handle.net/10919/40075.

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Hillier, Michael Campion. "The intramolecular cyclopropanation reaction and its application towards the synthesis of pseudopeptides and natural products /." Digital version accessible at:, 1999. http://wwwlib.umi.com/cr/utexas/main.

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39

Grech, Jason Mark. "The synthetic applications of organomercurials arising by the cleavage of cyclopropane derivatives." Thesis, University of Leicester, 1996. http://hdl.handle.net/2381/33701.

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Organomercurial esters 2a-c obtained from cyclopropyl alcohols la-c in three or five (depending on whether the system is cis or trans) steps, react with organocuprates via an intramolecular addition across the carbonyl bond to generate the corresponding lactolate. Quenching of the latter intermediate with water leads to the lactol 3a, c in the cycloheptane and cyclopentane series, whereas the open hydroxyketone 4b is formed in the cyclohexane series. Quenching of the lactolate with BF3 Et2O gives different products, as demonstrated for the cyclohexane series. The Pd(II)-catalysed carbonylation of chloromercurio alcohols 5a-c allows the construction of either cis- or trans-fused lactone rings 6a-c. The stereochemistry of the lactone annulation is controlled by the Hg (II) reagent to initially open the cyclopropane ring, in conjunction with oithogonal protection.

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40

Fleming, Alison A. "Synthesis and rearrangements of vinylcyclopropanes in a [2+3] cyclopentene and oxycyclopentene annulation methodology approach to (-)- specionin." Diss., Virginia Polytechnic Institute and State University, 1989. http://hdl.handle.net/10919/54358.

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The addition of lithium dienolate 130, formed from ethyl 2-bromocrotonate, to enones and aldehydes yielding vinylcyclopropanes and vinyloxiranes was optimized. Various methods, pyrolytic and nonpyrolytic, were examined for the rearrangement of the resulting vinylcyclopropanes to cyclopentenes in an overall [2+3] annulation sequence. During the course of these studies, a new rearrangement pathway of these vinylcyclopropanes to bridged [3.2.n] bicyclic systems was discovered thus establishing a new [3+4] annulation technology. The extension of the [2+3] annulation technology to oxygenated cyclopentanoids was addressed. Several ethyl 2-bromo-4-oxycrotonates were synthesized, and the reaction of their lithium dienolates (217) with enones was investigated. The rearrangement of the resulting enol ether terminated vinylcyclopropanes to oxygenated cyclopentenes was also examined. [see document for diagram of chemical reaction] The application of this methodology was expressed in a synthetic approach to (-)-specionin (109). The key steps in this synthesis involved the cyclopropanation of optically pure enone 147 with Iithium dienolate 155 to give vinylcyclopropanes 169-exo/endo and the rearrangement of 169 to the oxygenated cyclopentanoid 187-exo which possesses the correct stereochemistry for further elaboration to epoxy acetate 216, an intermediate in a reported synthesis of specionin. [see document for diagrams of chemical reactions]
Ph. D.

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41

Le, Gall Lefas Marie. "Synthese et proprietes biologiques de derives beta-substitutes ou cyclopropaniques de ligands melatoninergiques." Paris 11, 1998. http://www.theses.fr/1998PA114850.

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42

ISARNO, THOMAS. "Synthese asymetrique d'epoxydes et de cyclopropanes via des ylures de soufre chiraux. Utilisation de bases phosphazenes." Université Louis Pasteur (Strasbourg) (1971-2008), 2000. http://www.theses.fr/2000STR13023.

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Le travail decrit dans ce memoire porte sur la synthese asymetrique d'epoxydes et de cyclopropanes enantiomeriquement enrichis au depart d'ylures de soufre chiraux derives du (+)-(r,r,r)-oxathiane d'eliel. Les sels de sulfonium correspondants, aisement obtenus notamment grace a l'emploi de triflate d'argent, sont deprotones a l'aide de bases phosphazenes, deja utilisees avec succes lors d'additions de michael asymetriques en quantites catalytiques de base. Dans un premier temps les ylures ainsi obtenus ont ete mis en reaction avec des aldehydes aromatiques afin de generer des epoxydes diaromatiques avec des exces enantiomeriques entre 97 et 99. 8% et de configuration absolue r,r. L'emploi d'une base phosphazene notamment et-p 2 a permis de diminuer les temps de reaction a 30 minutes par rapport a 24-48h avec des bases classiques. L'ouverture d'un de ces epoxydes a permis d'obtenir un alcool pyridinique avec un exces enantiomerique de 99. 6% tres important en catalyse asymetrique homogene. Dans un deuxieme temps nous avons montre que cette methode etait applicable a la synthese d'arylcarbethoxycyclopropanes de configuration absolue r,r avec des exces enantiomeriques allant de 95 a 99% et des temps de reaction inferieurs a 30 minutes. Par ailleurs une etude rmn complete sur l'attribution cis/trans de ce type de cyclopropane a ete conduite. Nous avons egalement realise la premiere synthese asymetrique de nitrocyclopropanes par reaction avec des nitroalcenes. Enfin l'ouverture d'un cyclopropane portant un groupement tertbutyle, maintenant obtenu avec un exces enantiomerique de 98. 9% a permis la premiere synthese asymetrique du fenpropimorph, un fongicide puissant.

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43

Yet, Larry. "Chapter I: Synthesis and Chemistry of 1-(Benzenesulfonyl)-2- (Trimethylsilyl)Cyclopropane : Chapter II: 1,1-(Dilithio)-1- (Benzenesulfonyl)-2-(Trimethylsilyl)Ethane as an Effective Synthetic Equivalent for Symmetrical.. /." The Ohio State University, 1995. http://rave.ohiolink.edu/etdc/view?acc_num=osu1487864986611748.

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44

RECHSTEINER, BENNO. "Reactions organiques sans solvant activees par les microondes : application a la synthese d'enaminocetones, imidazolines, oxazolines et cyclopropanes." Rennes 1, 1994. http://www.theses.fr/1994REN10030.

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La premiere partie de ce travail est relative a la condensation de derives dicarbonyles avec les amines primaires et secondaires sans solvant et sous activation par les microondes. Cette reaction effectuee dans des recipients ouverts a une puissance d'irradiation determinee, conduit en quelques minutes a des enaminocetones avec d'excellents rendements. L'utilisation de recipients fermes entraine la formation d'acylamines. Dans la deuxieme partie, nous avons etendu notre etude a la condensation de diamines avec les composes dicarbonyles. Nous avons egalement mis en evidence l'influence des conditions d'irradiation sur l'evolution de la reaction. Ce travail nous a conduit a synthetiser des di-enaminocetones, imidazolines, oxazolines et sels de tetrahydro diazepine dont les mecanismes de formation sont discutes. Enfin dans une troisieme partie nous avons etudie la reactivite du diazoacetate d'ethyle vis-a-vis d'alcenes dans des conditions permettant la cycloaddition dipolaire 1,3 et d'autre part dans des conditions de formation de carbenes pour realiser la synthese de cyclopropanes, en solution, sous irradiation dans un four microondes adapte pour travailler en toute securite

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45

朱煒章 and Wai-cheung Chu. "Syntheses and reactions of copper and manganese complexes of tetradentate polyanionic chelating ligands and their applications incarbon-heteroatom bond formation reactions." Thesis, The University of Hong Kong (Pokfulam, Hong Kong), 1997. http://hub.hku.hk/bib/B31236789.

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Chu, Wai-cheung. "Syntheses and reactions of copper and manganese complexes of tetradentate polyanionic chelating ligands and their applications in carbon-heteroatom bond formation reactions /." Hong Kong : University of Hong Kong, 1997. http://sunzi.lib.hku.hk/hkuto/record.jsp?B19324893.

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47

Glass, Adam Cameron 1983. "The Synthesis of Novel and Sterically Demanding Tetra-ortho-substituted Aryl Naphthalenes." Thesis, University of Oregon, 2011. http://hdl.handle.net/1794/11978.

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xiv, 326 p. : ill. (some col.)
Tetra-ortho -substituted aryl naphthalenes (TOANs) are a motif of great importance, being present in biologically active natural products, chiral ligands, and building blocks relevant to materials science. The synthesis of sterically demanding and enantioenriched TOANs continues to be a challenge for current synthetic methods. Herein, we describe the highly effective synthesis of a variety of sterically demanding and enantioenriched TOANs through a rearrangement-based method. Our method utilizes a cyclopropyl carbinol moiety as the key rearrangement precursor. We have demonstrated that carbon-carbon coupling through a simple nucleophilic attack on a cyclopropyl indanone allows for very large aryl substrates to be added and rearranged. We discuss in detail the following: 1) the initial substrate-scope and proof-of-concept studies, 2) our progress in building the most sterically demanding TOANs to date, and 3) the asymmetric synthesis of TOANs through chiral transfer. This dissertation includes previously published and unpublished co-authored material.
Committee in charge: Michael M. Haley, Chairperson; Shih-Yuan Liu, Advisor; Darren W. Johnson, Member; Victoria J. DeRose, Member; Paul J. Wallace, Outside Member

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48

Hewitt, Russell James. "Investigations of ring-opening reactions of cyclopropanated carbohydrates : towards the synthesis of the natural product (--)-TAN-2483B : a thesis submitted to the Victoria University of Wellington in fulfilment of the requirements for the degree of Doctor of Philosophy in Chemistry /." ResearchArchive@Victoria e-Thesis, 2010. http://hdl.handle.net/10063/1249.

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49

Kan, Tze-wai Jovi, and 簡紫慧. "Development of new polymer-supported reagents for organic synthesis, solvent effects in samarium promoted allylic alcohol cyclopropanationreactions and time resolved resonance studies of the photodeprotectionof p-hydroxyphenacyl caged phototrigger compounds." Thesis, The University of Hong Kong (Pokfulam, Hong Kong), 2006. http://hub.hku.hk/bib/B37925660.

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50

Denis, Alexis. "Fonctionnalisations selectives a l'aide des complexes du palladium : synthese de composes d'interet biologiques, cyclopropanes vinyliques, aryl-3 oxazolidinones-2 (inhibiteurs potentiels de la monoamine oxydase)." Paris 6, 1987. http://www.theses.fr/1987PA066335.

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Ce travail porte sur l'utilisation du palladium (o) pour la synthese de molecules d'interet biologique. En premier lieu, on decrit la synthese stereoselective de cyclopropanes vinyliques et de pyrethrinoides. Dans un second temps, on etudie l'echange acetate phenol et l'amination de derives allyliques fibonctionnels. Enfin, on presente la synthese d'aryl-3 dihydroxy-5,5 oxazolidones-2 erythro et threo et etudie leur utilisation en tant qu'inhibiteur d'enzyme monoamine oxidase

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