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Dissertations / Theses on the topic 'Homochiral synthesis'

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Published: 4 June 2021
Last updated: 15 February 2022

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1

Wyatt, Paul Jeffery. "Homochiral phosphepin oxides." Thesis, University of Cambridge, 1995. https://www.repository.cam.ac.uk/handle/1810/272998.

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2

Mwaniki, Joseph Mugambi. "Synthesis of homochiral propargylsilanes." Thesis, University of Cambridge, 1998. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.624664.

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3

Golighar, Abdul Munaff. "The synthesis of homochiral polythiophenes." Thesis, Bangor University, 1995. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.262594.

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4

Gerhard, A. U. "Synthesis of homochiral thiazolium catalysts." Thesis, University of Cambridge, 1997. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.599363.

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This thesis describes the synthesis of six bicyclic homochiral thiazolium salts for the catalysis of certain carbon-carbon bond formation reactions in an asymmetric manner. The synthesis of chiral thiazolium salts has been described in the literature previously. However, these catalysts gave either high chemical yields and low enantiomeric excess or low chemical yields and only moderate asymmetric induction in the carbon-carbon bond formation reaction. The synthesis of the rigid bicyclic thiazolium salts was attempted by the well-known α-haloketone route. This failed to yield the corresponding thiazolium salt because attempts to synthesise the α-haloketones of the bicyclo[2.2.1]heptane series gave only Wagner-Meerwein rearranged β-haloalcohols. The synthesis of the α-bromoketone of the bicyclo[2.2.2]octane series, however, was successful. Unfortunately, it did not react with thiocarbamates or thioformamide to give the desired thiazolium salts, probably due to steric congestion. Alternatively, thiazoles can be formed via the α-aminoketone route. The thiazoles were prepared in a three step synthesis, starting from bicyclic[2.2.2]octane silyl enol ethers in up to 35% yields. The silyl enol ethers were then converted into the α-ketooximes followed by reduction, formylation and thiocyclisation to give the desired thiazoles. The enantiomers of the thiazoles were separated by fractional recrystallisation of their diastereomeric salts with (R)- or (S)-camphorsulfonic acid. The homochiral thiazoles were then converted into the corresponding methyl and benzyl thiazolium salts. The catalysts were tested in the benzoin condensation to give benzoin, and in the dimerisation of butyraldehyde to produce butyroin. Benzoin was formed in up to 100% chemical yield and up to 25% e.e. For the first time, asymmetric induction was observed in the dimerisation of aliphatic aldehydes catalysed by thiazolium salts. Butyroin was formed in up to 70% chemical yield by only 8% e.e.
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5

Mantell, Simon J. "Synthesis of highly functionalised homochiral compounds." Thesis, University of Oxford, 1993. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.334895.

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6

Miller, Andrew Philip. "Homochiral amine oxides in organic synthesis." Thesis, University of Liverpool, 1998. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.365894.

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7

Preston, Simon Christopher. "Asymmetric synthesis via iron acyl complexes." Thesis, University of Oxford, 1989. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.236153.

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8

Case-Green, S. C. "Double asymmetric synthesis." Thesis, University of Oxford, 1991. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.293361.

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9

Buffet, Jean-Charles. "Homochiral metal complexes for biodegradable polymer synthesis." Thesis, University of Edinburgh, 2010. http://hdl.handle.net/1842/4618.

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Chapter One introduces the principle of alkoxide and phosphine oxide as ligands for lanthanides and electropositive metals, ligand self-recognition, stereoselective polymerisation of lactide, fixation of CO2 and finally copolymerisation of CO2 and epoxide. Chapter Two shows the synthesis of the proligands rac-HLR (a racemic phosphine oxide-alkoxide, A, where R = tBu, Ph or C6H3-Me-3,5) and explores the resolution into diastereomeric RRR- and SSS-M(LR)3 to afford C3–symmetric M(LR)3 complexes, B (where M = Sc, Lu, Y, In, Bi or La). It also demonstrates that the process is under thermodynamic control and driven by ligand self-recognition via the synthesis of bis(LR) adducts (LR)2MX, C, (where M = Y or In and X = N(SiMe3)2 or OC6H3-tBu2-2,6) and mono(LR) adducts (LR)MX2, D (where M = Al or In and X = N(SiMe3)2, CH2SiMe3 or Me). Finally, it outlines the fixation of CO2 into an indiumamide bond. Chapter Three contains a detailed investigation of the potential of the MIII complexes as initiators for the stereoselective polymerisation of lactide, - caprolactone, glycolide and copolymerisation of lactide and -caprolactone, lactide and glycolide and CO2 and epoxide. Chapter Four investigates the use of rac-HLtBu in the resolution into diastereomeric RR- and SS-M(LtBu)2 complexes, E (where M = Ca, Zn or Sn), and of rac-HLPh into [M(LR)2]2 complexes, F (where M = Mg, Co or Sn and R = Ph or C6H3-Me-3,5) and mono-(LtBu) adducts (LtBu)MgX, G (X = N(SiMe3)2 or OC6H3-tBu2-2,6). It also describes the synthesis of protonated MII complexes (HLR)MCl2, H (where M = Mg, Zn or Sn and R = tBu or Ph). Finally, it details the polymerisation of lactide and its copolymerisation with glycolide using MII complexes as initiators. Chapter Five gives full experimental details and analytical data for the herein described novel compounds.
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10

Ginnelly, Michael John. "Synthesis and applications of homochiral phosphepin oxides." Thesis, University of Cambridge, 2000. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.621880.

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11

Birchall, Andrew Carl. "The synthesis of novel homochiral polymers from amino acids." Thesis, Bangor University, 1999. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.310924.

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12

Howard, Kevin James. "1,3-dipolar cycloadditions : a new synthesis of homochiral pyrrolidines." Thesis, University of Nottingham, 1995. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.282678.

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13

Rae, Alastair. "New methodology for the synthesis of homochiral unsaturated amines." Thesis, University College London (University of London), 1998. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.300661.

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14

Persad, Andrew B. "Applications of homochiral lithium amide bases to sulphones and sulphoxides." Thesis, University of Nottingham, 1993. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.334775.

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15

Crump, Roger Adrian Neil Callow. "Enantio- and diastereocontrol with silicon compounds in organic synthesis." Thesis, University of Cambridge, 1993. https://www.repository.cam.ac.uk/handle/1810/272577.

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16

McCarthy, Noreen. "Catalytic asymmetric synthesis and homochiral transformations using #alpha#-diazocarbonyl intermediates." Thesis, Queen's University Belfast, 1993. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.333843.

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17

Bailey, David John. "The Synthesis of homochiral ligandsand their application to asymmetric fluorinating reagents." Thesis, Durham University, 1994. http://etheses.dur.ac.uk/5672/.

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This thesis is concerned with the synthesis of homochiral ligands and their application to asymmetric fluorinations. Initial work focused on the synthesis of homochiral pyridine based ligands and the determination of their optical purity. 2-Acetylpyridine was reduced using bakers' yeast in the presence of an enzyme inhibitor to give a homochiral pyridyl alcohol. A double asymmetric reduction of 2,6-diacetylpyridine was also achieved using bakers' yeast and the resulting diol was also found to be homochiral. Derivatives of the above pyridyl alcohols were then reacted with 10% F2/N2 in the presence of a suitable counterion to form N-fluoropyridinium salts. These reagents were then used to fluorinate a range of silyl ketene acetals and metal enolates to assess their ability as asymmetric electrophilic fluorinating reagents. Although the reagents achieved fluorination, they were found to be poor asymmetric fluorinating reagents. A new synthetic route into the pyrrolidine based amine (2S)-(diphenyl)methylpyrrolidine was developed and its use in a number of asymmetric transformations was investigated. Both DAST and Ishikawa's reagent have proved successful in achieving the replacement of alcohol hydroxyl groups by fluorine. Development of a nucleophilic asymmetric fluorinating reagent based on DAST and Ishikawa's reagent was attempted using (2S)-(diphenyl)methylpyrrolidine as the precursor amine. The homochiral derivatives of DAST and Ishikawa's reagent which were developed, only achieved limited success as fluorinating reagents and the fluorinated products were found to be racemic.(2S)-(Diphenyl)methylpyrrolidine was also found to act as a chiral solvating reagent with certain carboxylic acids and alcohols, these showing chemical non-equivalence by NMK Two (2S)-(diphenyl)methylpyrrolidine units were also coupled together by a two and three carbon bridge forming two novel diamines. Initial studies on the ability of these amines to act as asymmetric catalysts in dihydroxylation reactions using osmium tetroxide and asymmetric addition reactions of Grignard reagents to aldehydes are also described.
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18

Andrew, Adam Lee. "The application of homochiral tertiary amine N-oxides in organic synthesis." Thesis, University of Liverpool, 2002. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.272631.

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19

Crawforth, James Michael. "Homochiral synthesis of paraconic acid and the biosynthesis of amphotericin B." Thesis, University of Leicester, 1996. http://hdl.handle.net/2381/34068.

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Homochiral (S)-(-)-paraconic acid was synthesised in 18% overall yield from (45)-4-isopropyl-2-oxazolidinone using titanium enolate methodology. Paraconic acid was used to synthesise A-factor. A-factor and analogues were fed to a culture of Streptomyces nodosus however no definitive enhancement, or a decrease in the lag time for the onset of metabolite production was observed. Sodium acetate-d3, [1-13C] and [3-13C]-propionate were fed to a culture of Streptomyces nodosus and label incorporation into amphotericin B of 10-15% was observed.
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20

Math, Shivanand Kumarswamy, and Shivanand Kumarswamy Math. "Diastereoselective cyclopropanation of medium and large ring alpha, beta-unsaturated homochiral ketals and enantioselective synthesis of (-)-modhephene." Diss., The University of Arizona, 1989. http://hdl.handle.net/10150/184664.

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A general straightforward synthetic approach for the enantioselective construction of medium and large ring cyclopropyl ketones via diastereoselective Simmons-Smith cyclopropanation is discussed. Medium and large 2-cycloalkenone 1,4Di-O-benzyl-L-threitol ketals undergo efficient and diastereoselective cyclopropanation when treated with an excess of the Simmons-Smith reagent. The cyclopropyl ketals are obtained in 80-94% with >23:1-8:1 diastereoselectivity. The first enantioselective synthesis of (-)-modhephene, a natural product possessing the carbocyclic (3.3.3) propellane skeleton, by the use of diastereoselective cyclopropanation methodology is described.
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21

Tavasli, Mustafa. "Synthesis of a new class of homochiral amines and novel bio-active tropanes." Thesis, Durham University, 1999. http://etheses.dur.ac.uk/4552/.

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This thesis describes two main programmes: the synthesis of a new class of homochiral amines and the synthesis of ketone analogues of 3a-esterified tropane alkaloids. In chapter one, a scaled-up synthesis of (5)-a-(diphenylmethyl)pyrrolidine 1 is described. The key hydrogenation step of the oxazolidinone intermediate 2 was extended to the synthesis of the other chiral amines 70, 73, 76, 79 and 82. Hydrogenation of the oxazolidinones proceeded in good yields (71 - 87 %) and was not susceptible to racemisation. Thus, a convenient route from amino acid ester hydrochlorides (S)-valine 65, (S)-phenylalanine 66, (S)-alanine 67, (S)-isoleucine 68 and (S)-leucine 69 allowed a range of novel chiral amines to be prepared. In chapters two and three, a new route to ketone analogues of tropane esters is described. In chapter two, results of an attempt to prepare ketone 110 are outlined. Ketone 110 is an analogue of the tropane alkaloid littorine 101, where the bridging ester O atom is replaced by a CH2 group. The first approach to ketone 110 involved the Wittig reaction of acetylmethylenephosphorane 118 and the Homer-Wadsworth- Emmons reaction of diethylbenzoylmethanephosphonate 122 with tropinone 116. Tropinone 116 was found to be particularly unreactive in both cases. The second approach to ketone 110 involved the coupling reactions of both N-troc-3a- tosyloxymethyltropane 170 and N-troc-3 a-iodomethyltropane 185 with 2-phenylacetyl- 1,3-dithiane 147 and 1,3-ditihiane 142. These were also unreactive and as a result the synthesis of ketone 110 remains unresolved. In chapter three, the synthesis of other ketone analogues of naturally occurring 3 a- esterified tropane alkaloids is described. A six-step route to the ketones was devised and in this route the Grignard reactions of tropan-3 -ylacetaldehyde 227 emerged as the key to the success of the strategy. Three ketone analogues 218, 219 and 220 of tropate esters were successfully prepared. Ketone 220, the analogue of apoatropine 201, was found to be a muscarinic acetylcholine receptor antagonist (EC(_50) 1.9x10(^-7) M) in guinea-pigileum, showing a 500-fold less activity than atropine 202. However the activity is still within the clinical range.
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22

Jawaid, Samaila. "Asymmetric synthesis of 2-substituted butane-1,4-diols by hydrogenation of homochiral fumaramide derivatives." Thesis, University of Glasgow, 2005. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.412945.

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23

Hemperly, Susan Barbara. "Mechanistic studies of diastereoselective cyclopropanations of homochiral ene-ketals and synthesis and resolution of diastereomeric alpha-hydroxycycloalkanone ketals." Diss., The University of Arizona, 1989. http://hdl.handle.net/10150/184886.

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A series of homochiral ene ketals were prepared and subjected to the Simmons-Smith cyclopropanation. A mechanistic model was formulated to explain the observed diastereoselectivity seen for the common ring systems. Diastereoselectivity is thought to result from preferential chelation of the Simmons-Smith reagent at the least sterically hindered lone pair of electrons on the dioxolane oxygen proximal to the alkene. The role of dioxolane oxygen was inferred from studies with a hydrocarbon model system. The effect of cyclohexene ring conformation on the diastereoselectivity was examined for conformationally restricted ene ketal systems. Reagent chelation by the pseudoequatorial dioxolane oxygen atom was shown to be favored. This preference can either antagonize or reinforce diastereoselectivity due to steric hindrance of the dioxolane oxygen atoms from dissymmetric placement of the appendages on the dioxolane ring. A general method for the chromatographic resolution of diastereomeric α-hydroxycycloalkanone ketals derived from 1,4-di-O-benzyl-L-threitol is reported. Separability is thought to result from differences in intramolecular hydrogen bonding for the two diastereomeric forms.
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24

Zhang, Shi-Yuan. "Homochiral Metal-Organic Materials: Design, Synthetic and Enantioseletive Separation." Scholar Commons, 2014. https://scholarcommons.usf.edu/etd/5163.

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Owing to the growing demand for enantiopurity in biological and chemical processes, tremendous efforts have been devoted to the synthesis of homochiral metal-organic materials (MOMs) because of their potential applications in chiral separation and asymmetric catalysis. In this dissertation, the synthetic strategies for homochiral MOMs are discussed keeping the focus on their applications. Two distinct approaches have been taken to synthesize chiral structures with different topologies and accessible cavities. The chiral MOMs have been utilized in enantioselective separation of racemates. Chiral variants of the prototypal metal-organic framework MOF-5, δ-CMOF-5 and [lambda]-CMOF-5, have been synthesized by preparing MOF-5 in the presence of L-proline or D-proline, respectively. CMOF-5 crystallizes in chiral space group P213 instead of Fm-3m as exhibited by MOF-5. The phase purity of CMOF-5 was validated by single crystal and powder X-ray diffraction, IR spectroscopy, TGA, N2 adsorption, microanalysis and solid-state CD. CMOF-5 undergoes a reversible single crystal to single crystal phase change to MOF-5 when immersed in a variety of organic solvents although N-methyl-2-pyrolidone, NMP, does not induce loss of chirality. Indeed, MOF-5 undergoes chiral induction when immersed in NMP, affording racemic CMOF-5. A pair of homochiral network materials (CNMs), [Co2(S-man)2(bpy)3](NO3)2·guests (1S) and [Co2(R-man)2(bpy)3](NO3)2·guests (1R) based upon S-mendelic acid and R-mendelic acid were synthesized and characterized, respectively. The cationic networks contain 1D homochiral channels with the cross section of 8.0 Å × 8.0 Å. The chiral amphiphilic channel surfaces lined with hydrophilic nitrate anions and hydrophobic phenyl groups are capable for multiple interactions with guest species. Chiral resolution of 1-phenyl-1-propanol (PP) enantiomers was performed utilizing the homochiral porosity of 1S and 1R through different time period at different temperatures with/without additives. The mechanism for enantioselective separation of PP was fully investigated through single crystal structural analysis of guest exchanged 1S and 1R. Chiral resolution of PP revealed enhanced performance with additive, which can significantly improve the ee value from 32% to 60%.
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25

Feske, Brent D. "Synthetic applications of homochiral glycidic esters derived from enzymatic reductions." [Gainesville, Fla.] : University of Florida, 2005. http://purl.fcla.edu/fcla/etd/UFE0012081.

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26

PORTAL, MARTINE. "Syntheses de pyrrolidines et azetidines polyfonctionnalisees homochirales d'interet biologique." Paris 6, 1993. http://www.theses.fr/1993PA066211.

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Les pyrrolidines polyhydroxylees chirales jouent un role biologique important en agissant principalement comme inhibiteurs de glycosidases, antibiotiques, antidiabetiques, insecticides. L'acces aux pyrrolidines et aux azetidines polyhydroxylees a ete realise a partir de produits naturels peu onereux. Dans le chapitre i, nous presentons la synthese du 2,5-dideoxy-2,5-imino-d-mannitol (dmdp, inhibiteur de glucosidases) et d'un diastereoisomere, le 2,5-dideoxy-2,5-imino-l-iditol, a partir du seul d-mannitol. Dans le chapitre ii, nous presentons la synthese de l'acide 3-hydroxy-azetidine-2-carboxylique, -amino acide non proteinique et unite chirale, composante de l'acide 3-hydroxymugineique (phytosiderophore) ainsi que l'aldehyde correspondant, a partir du diethyl-l-tartrate. Enfin, dans le chapitre iii, nous proposons la synthese d'un precurseur de la (-) anisomycine (antibiotique) a partir du l-arabinose
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27

Jin, Jing. "A Cooperative Pillar-Template Strategy as a Generalized Synthetic Method for Flexible Homochiral Porous Frameworks." Thesis, California State University, Long Beach, 2018. http://pqdtopen.proquest.com/#viewpdf?dispub=10840741.

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A new strategy for creating homochiral metal-organic frameworks is demonstrated, through fusion of pillaring and templating concepts. This strategy makes use of the synergy among various chemical interactions during self-assembly process, and leads to the synthesis of a series of homochiral frameworks. In the presence of only pillar-to-pillar π-π interactions, inter-pillar forces compete again metal-pillar interactions, resulting in mismatch between pillar-to-pillar and metal-to-metal separations and consequently 2-D materials without pillaring. To create 3-D materials, a method is developed to use various aromatic molecules, polycyclic aromatic hydrocarbons in particular, as templates to modulate the inter-pillar interaction and separation, leading to the formation of 3-D homochiral frameworks. The use of aromatic molecules, especially hydrocarbons, as structure-directing agents, represents a new approach in the development of crystalline porous materials. Aromatic templates can be post-synthetically extracted to yield flexible porous homochiral materials with gate-opening gas sorption behaviors for both N2 and CO2 at partial pressures tunable by temperatures.

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28

Seck, Matar. "Preparation de dihydrofurannes et tetrahydrofurannes homochiraux. Applications a la synthese de substances naturelles." Paris 11, 1991. http://www.theses.fr/1991PA112062.

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Le travail rapporte dans ce memoire de these concerne d'une part la mise au point d'une nouvelle methodologie permettant l'acces a des dihydrofurannes et tetrahydrofurannes homochiraux substitues en position 2 et d'autre part l'utilisation de ces composes pour la synthese de substances naturelles biologiquement actives. L'encombrement sterique du groupement protecteur de la double liaison d'un gamma-lactol a permis de realiser des reactions tandem wittig-horner/michael intramoleculaire tres stereoselectives. La deprotection de la double liaison par reaction de retro diels-alder donne acces aux dihydrofurannes. A partir d'un lactol enantiomeriquement pur, obtenu par voie enzymatique, cette methodologie a ete appliquee a la synthese de lactones a 5 chainons: le (r)-4-methoxycarbonylmethyl-2-butenolide antipode d'une substance cytotoxique extraite d'une eponge marine et l'eldanolide, pheromone sexuelle d'eldana saccharina. L'etude de l'ouverture regioselective de dihydrofurannes et tetrahydrofurannes obtenus selon la methodologie developpee dans la premiere partie, a conduit a une methode d'acces aux diols-1,3 primaires secondaires ou secondaires secondaires. L'interet de cette methode est illustre par la synthese de substances naturelles: un diol precurseur de l'acide lipoique et le (-)(1r,3r,5s)-1,3-dimethyl-2,9-dioxabicyclo 3. 3. 1 nonane: pheromone sexuelle du scarabee trypodendron lineatum oliver
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29

森, 敦紀, and Atsunori Mori. "ASYMMETRIC SYNTHESIS USING HOMOCHIRAL ACETAL." Thesis, 1987. http://hdl.handle.net/2237/12558.

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30

"ASYMMETRIC SYNTHESIS USING HOMOCHIRAL ACETAL." Thesis, 1987. http://hdl.handle.net/2237/12558.

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31

Chiu, Hsiao-shan, and 邱筱珊. "Synthesis, Characterization and Crystal Engineering Structural Transformation of L-Thiazolidine-4-carboxylate-containing Homochiral Coordination Compounds." Thesis, 2013. http://ndltd.ncl.edu.tw/handle/28282970174106855902.

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碩士
國立中央大學
化學學系
101
This thesis focuses on the preparation of a series of metal complexes via the use of a combination of metal (Zn(II), Co(II), Ni(II), Cd(II) salts with a LTP (L-thiazolidine-4-carboxylate)) ligand under mild reaction conditions. Their structures were characterized by single-crystal X-ray diffraction analyses. The structures of the first series [M(LTP)2(H2O)2] (M = Zn(II) 1, Co(II) 2, Ni(II) 3) show that the metal ion is six-coordinated in a distorted octahedral geometry and bonded to two N and two O atoms from two LTP ligands with bis-chelating coordination mode and two water molecules. Hydrogen bonding interactions between the LTP ligand and the water molecule were observed to play an important role in the formation of their 3D hydrogen-bonded supramolecular architectures. The metal ion in the second series [M(LTP)2]n (M = Zn(II) 4) is five-coordinated, with a distorted trigonal bipyramidal geometry, bonded to two N and three O atoms from three LTP ligands. The metal ion in the third series of compounds [M(LTP)2]n (M = Zn(II) 5, Cd(II) 6) is six-coordinated in a distorted octahedral geometry, bonded to two N and four O atoms from four LTP ligands. In 4, one LTP ligand acts as a monodentate coordination mode through an O atom and the other two LTP ligands act as bis-chelating coordination modes through both N and O atoms with a metal ion to form a one-dimensional (1D) [Zn(LTP)2] chain. In 5 and 6, the two LTP ligands act as chelating agents through both N and O atoms and the other two LTP ligands are coordinated with metal ions via an O atom to form a two-dimensional (2D) wave-like network. These 2D layers are then arranged in an ABAB-type array via the intermolecular interactions of N-H×××S hydrogen bonds to form a 3D supramolecular architecture. The thermal stability of compounds 1-6 are studied by TGA analysis. In addition, in-situ PXRD measurements verify that the crystal engineering transformation of 1 to 4 and 1 to 5 in a major and minor product, respectively.
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