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Littérature scientifique sur le sujet « Enantioselective synthesi »

Auteur : Grafiati

Publié le 9 mars 2023

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Articles de revues sur le sujet "Enantioselective synthesi"

Gualandi, Andrea, Luca Mengozzi et Pier Cozzi. « Stereoselective SN1-Type Reaction of Enols and Enolates ». Synthesis 49, n^o 15 (13 juin 2017) : 3433–43. http://dx.doi.org/10.1055/s-0036-1588871.

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Stereoselective alkylation of enolates represents a valuable and important procedure for accessing carbon–carbon-bond frameworks in natural and nonnatural product synthesis. Usually, activated electrophilic partners that react through an SN2 mechanism are employed. To overcome the limitations due to reduced reactivity and steric hindrance, SN1-type reactions can be considered a valid and practical alternative. Accessible enolates can be used in stereoselective (diastereo- or enantioselective) reactions with electrophilic carbenium ions, either used as stable reagents or generated in situ from suitable precursors. The results achieved in this active field are summarized in this review.1 Introduction2 Alcohols in SN1-Type Reactions with Enolates2.1 Enantioselective Reactions with Metal Complexes2.2 Organocatalytic Enantioselective Reactions3 Alcohols and Alcohol Derivatives in SN1-Type Reactions with Enolates: Enantioselective Reactions with Metal Enolates4 Isolated Carbenium Ions in SN1-Type Reactions with Enolates: Enantioselective Reactions with Metal Enolates5 Miscellaneous6 Conclusion

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Du, Kang, He Yang, Pan Guo, Liang Feng, Guangqing Xu, Qinghai Zhou, Lung Wa Chung et Wenjun Tang. « Efficient syntheses of (−)-crinine and (−)-aspidospermidine, and the formal synthesis of (−)-minfiensine by enantioselective intramolecular dearomative cyclization ». Chemical Science 8, n^o 9 (2017) : 6247–56. http://dx.doi.org/10.1039/c7sc01859b.

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Palladium-catalyzed enantioselective dearomative cyclization has enabled the concise and enantioselective total syntheses of (−)-crinine and (−)-aspidospermidine, as well as a formal total synthesis of (−)-minfiensine.

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Enders, Dieter, et Christoph Thiebes. « Efficient stereoselective syntheses of piperidine, pyrrolidine, and indolizidine alkaloids ». Pure and Applied Chemistry 73, n^o 3 (1 janvier 2001) : 573–78. http://dx.doi.org/10.1351/pac200173030573.

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Recent advances in the diastereo- and enantioselective synthesis of piperidine, pyrrolidine, and indolizidine alkaloids, based on the highly stereoselective 1,2-addition to the CN double bond of chiral aldehyde-SAMP/RAMP hydrazones, are described. The enantioselective syntheses of the pyrrolidine alkaloids bgugaine and (2S,12¢R)-2-(12¢-aminotridecyl)-pyrrolidine, a defense alkaloid of the Mexican bean beetle are reported. Furthermore, the SAMP/RAMP-hydrazone method was applied to the syntheses of two 5,8-disubstituted indolizidine alkaloids that have been extracted from neotropical poison-dart frogs. The a-alkylation of aldehyde-SAMP/RAMP hydrazones has been used in the enantioselective synthesis of two epimers of stenusine, a 3-substituted piperidine alkaloid and spreading reagent of the beetle Stenus comma.

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Chen, Bo, Xin Liu, Ya-Jian Hu, Dong-Mei Zhang, Lijuan Deng, Jieyu Lu, Long Min, Wen-Cai Ye et Chuang-Chuang Li. « Enantioselective total synthesis of (−)-colchicine, (+)-demecolcinone and metacolchicine : determination of the absolute configurations of the latter two alkaloids ». Chemical Science 8, n^o 7 (2017) : 4961–66. http://dx.doi.org/10.1039/c7sc01341h.

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Sundermann, Tom, Martina Arnsmann, Julian Schwarzkopf, Walburga Hanekamp et Matthias Lehr. « Convergent and enantioselective syntheses of cytosolic phospholipase A2α inhibiting N-(1-indazol-1-ylpropan-2-yl)carbamates ». Org. Biomol. Chem. 12, n^o 23 (2014) : 4021–30. http://dx.doi.org/10.1039/c4ob00535j.

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Sathish, Manda, Fabiane M. Nachtigall et Leonardo S. Santos. « Bifunctional thiosquaramide catalyzed asymmetric reduction of dihydro-β-carbolines and enantioselective synthesis of (−)-coerulescine and (−)-horsfiline by oxidative rearrangement ». RSC Advances 10, n^o 63 (2020) : 38672–77. http://dx.doi.org/10.1039/d0ra07705d.

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A simple and efficient asymmetric synthesis of THBCs through a chiral thiosquaramide 11b catalyzed imine reduction of dihydro-β-carbolines (17a−f) and syntheses of (−)-coerulescine and (–)-horsfiline via enantioselective oxidative rearrangement.

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Liu, Yiyang, Marc Liniger, Ryan M. McFadden, Jenny L. Roizen, Jacquie Malette, Corey M. Reeves, Douglas C. Behenna et al. « Formal total syntheses of classic natural product target molecules via palladium-catalyzed enantioselective alkylation ». Beilstein Journal of Organic Chemistry 10 (28 octobre 2014) : 2501–12. http://dx.doi.org/10.3762/bjoc.10.261.

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Pd-catalyzed enantioselective alkylation in conjunction with further synthetic elaboration enables the formal total syntheses of a number of “classic” natural product target molecules. This publication highlights recent methods for setting quaternary and tetrasubstituted tertiary carbon stereocenters to address the synthetic hurdles encountered over many decades across multiple compound classes spanning carbohydrate derivatives, terpenes, and alkaloids. These enantioselective methods will impact both academic and industrial settings, where the synthesis of stereogenic quaternary carbons is a continuing challenge.

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Zhang, Yun, Yibin Xue, Gang Li, Haosen Yuan et Tuoping Luo. « Enantioselective synthesis of Iboga alkaloids and vinblastine via rearrangements of quaternary ammoniums ». Chemical Science 7, n^o 8 (2016) : 5530–36. http://dx.doi.org/10.1039/c6sc00932h.

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We present an efficient and unified strategy for the enantioselective syntheses of various iboga alkaloids and vinblastine, involving gold-catalyzed oxidation and Stevens rearrangement. New vinblastine analogs were prepared by our 10-step synthesis.

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T. Mohd Ali, M., et . « Synthesis of -Hydroxy -Proline : Potential for Organocataly-sis Reactions ». International Journal of Engineering & ; Technology 7, n^o 4.14 (24 décembre 2019) : 237. http://dx.doi.org/10.14419/ijet.v7i4.14.27571.

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A chiral organic molecule, L-proline catalyzed an enantioselective transformation reaction has becoming interesting synthetic protocol especially in the area of organocatalysis. Herein, a synthetic approach towards -hydroxy--proline starting from bicyclic lactone lactam is hereby described. The syntheses utilized dicarboxylation reaction of bicyclic lacton lactam, followed by ether hydrolysis of the bicyclic ether and oxidation reaction of the primary alcohol. The synthetic strategy disclosed here allows further the enantioselective synthesis of a variety of unnatural amino acids based on -proline structure.

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Martin, Stephen F. « Ring-closing metathesis : A facile construct for alkaloid synthesis ». Pure and Applied Chemistry 77, n^o 7 (1 janvier 2005) : 1207–12. http://dx.doi.org/10.1351/pac200577071207.

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Ring-closing metathesis has been found to be a highly effective reaction for the synthesis of functionalized, bridged nitrogen heterocycles. The utility of the process has been established in several case studies, including a facile synthesis of the tropane ring system and efficient, enantioselective syntheses of the natural products (–)-peduncularine and (+)-anatoxin-a.

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Thèses sur le sujet "Enantioselective synthesi"

PELLICCIOLI, VALENTINA. « HETEROHELICENES AS APPEALING CHIRAL SYSTEMS : INNOVATIVE METHODOLOGIES FOR THEIR PREPARATION ALSO IN ENANTIOMERICALLY PURE FORM ». Doctoral thesis, Università degli Studi di Milano, 2021. http://hdl.handle.net/2434/820983.

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Helicenes are ortho-annulated polycyclic aromatic or heteroaromatic compounds, endowed with inherent chirality owing to the helical shape of their π-conjugated system. Carbohelicenes only include benzene rings in their structure, while in heterohelicenes one or more heterocycles are present. Interestingly, the introduction of heteroatoms into the fused polycyclic frameworks adds remarkable changes to the electronic structures of helicenes, and additional chemical and physical properties. Their unique structural features and physicochemical properties have stimulated manifold studies in several fields, including optoelectronics, material science, asymmetric catalysis, and chiral recognition. Many of these applications require the use of enantiomerically pure helicenes, although the resolution of racemates by means of analytical methods as well as the separation of diastereomers still remain the most common ways to obtain non-racemic helicenes, whose peculiar geometry makes them extremely difficult targets for stereoselective synthesis. This Ph.D. thesis was intended to provide a meaningful contribution in the development of innovative and versatile syntheses of heterohelicenes, also in enantiopure form, and has focused on the following main goals: 1. Study of methodologies for the synthesis of functionalised tetrathia[7]helicenes (7-THs). 2. Synthesis of different classes of thiahelicenes through methodologies set up for the preparation of 7-THs. 3. Enantioselective synthesis of thia[5]helicenes via Au-catalysed alkyne hydroarylation. In the course of this thesis, a sub-topic has also been developed: 4. Functionalisation of benzo[1,2-b:4,3-b']dithiophenes by Suzuki reactions in Deep Eutectic Solvents (DESs).

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Blessley, George Richard. « Enantioselective synthesis and reactivity of benzylic fluorides ». Thesis, University of Oxford, 2013. http://ora.ox.ac.uk/objects/uuid:72cd3684-a339-453c-a9e8-c976ff731a0e.

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Benzylic fluorides are attractive target molecules for medicinal chemistry, agrochemicals and materials chemistry. The enantioselective synthesis of benzylic fluorides is challenging and few general methods exist. This thesis describes several approaches to the synthesis of benzylic fluoride targets, including enantioselective processes. Chapter 1: Reviews the properties, uses and synthetic approaches to fluorinated molecules, with a particular focus on benzylic fluorides and enantioselective syntheses. Chapter 2: Describes the fluorination cyclisation of prochiral indole precursors. The use of catalytic amounts of a bis-cinchona alkaloid gave good enantioselectivities for the cyclisation. Alcohol, tosylamine, amide and carbamate pendant nucleophiles all cyclised successfully to give quaternary benzylic fluorides in moderate yields and with enantioselectivities up to 92%. The substrate scope of the reaction is described, as well as methodology for deprotection of cyclised nitrogen nucleophiles. Chapter 3: Details an investigation of the Pd catalysed substitution of polycyclic benzylic fluorides by a range of nucleophiles and their relative reactivity in comparison to oxygen leaving groups. Modification of the methodology to enable reaction of monocyclic substrate substitution was enabled by the use of a protic solvent. Chemoselective reaction conditions were identified for selective reaction of Bn-F or Ar-Cl bonds and comparative reactivity studies were undertaken. The feasibility of Pd(0)/(II) catalysed nucleophilic C-F bond formation was examined. Chapter 4: The development of the defluorination methodology from Chapter 3 for secondary substrates is described. The stereochemical course of defluorination was probed, showing that displacement of fluoride is mechanistically similar to that of oxygen leaving groups. A kinetic resolution with a low selectivity was developed for access to enantioenriched benzylic fluorides.

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Baxter, Andrew Douglas. « Enantioselective synthesis of aminotetralins : novel synthetic applications of amino acids ». Thesis, University of East Anglia, 1994. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.359328.

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Sikkander, Mohamed Inthikhab. « Enantioselective synthesis of (+)-majusculone ». Access to citation, abstract and download form provided by ProQuest Information and Learning Company ; downloadable PDF file, 46 p, 2007. http://proquest.umi.com/pqdweb?did=1253510231&sid=1&Fmt=2&clientId=8331&RQT=309&VName=PQD.

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Boyes, Scott Antony. « Enantioselective synthesis using bromoacetals ». Thesis, Sheffield Hallam University, 1998. http://shura.shu.ac.uk/19380/.

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A brief overview of why it is important to prepare a chiral compound as a specific enantiomer rather than as a racemate is discussed along with several general strategies on how they maybe prepared. The area of research into the preparation of racemic and enantiomerically pure arylpropanoic acids is briefly reviewed by reference to some of the more important synthons. Some of the more general procedures that have been developed for the construction of arylpropanoic acids are discussed. The preparation of substituted alkyl aryl ketones and their subsequent two step conversion into diastereomerically enriched dimethyl tartrate (S)-bromoalkyl aryl acetals is described. An investigation into the effects of solvent, source of anhydrous acid, workup procedure, source of bromine and temperature upon the bromination of these dimethyl tartrate acetals is discussed. Direct conversion of these diastereomerically enriched dimethyl tartrate (S)-bromoalkyl aryl acetals into enantiomerically pure (S)-bromoalkyl aryl ketones and their subsequent conversion into (S)-bromoalkyl aryl esters via a Baeyer-Villiger reaction is described. Hydrolysis of these (S)-bromoalkyl aryl esters followed by treatment with diazomethane afforded the corresponding methyl (S)-bromoalkyl esters with minimal racemisation, while treatment of these (S)-bromoalkyl aryl esters with an amine gave the corresponding amide with minimal racemisation. Reduction with sodium borohydride at low temperature of a (S)-bromoalkyl aryl ketone afforded exclusively the corresponding (1S,2S) alkyl aryl bromohydrin as predicted using the Felkin-Anh model. Stereospecific conversion of our diastereomerically enriched dimethyl tartrate (S)-bromoalkyl aryl acetals into (S)-arylcarboxylic acids using a silver promoted or solvent promoted rearrangement is discussed. Subsequent conversion of these (S)-arylcarboxylic acids into the corresponding Boc amide via a modified Curtius rearrangement is described. Possible further uses of dimethyl tartrate bromoacetals leading to the synthesis of highly functionalised lactones, lactols, epoxides, chiral diacids, diamines, chiral ligands, resolving agents etc are also discussed.

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Efremov, Ivan V. « Enantioselective total syntheses of Teubrevin G and Teubrevin H and studies toward the Enantioselective Total Synthesis of Vinigrol / ». The Ohio State University, 2001. http://rave.ohiolink.edu/etdc/view?acc_num=osu1486399160105875.

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CHABOCHE, CHRISTOPHE. « Synthese totale enantioselective d'acetogenines d'annonaceae ». Paris 11, 1996. http://www.theses.fr/1996PA114804.

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Azzouz, Mariam. « Enantioselective synthesis of natural products ». Doctoral thesis, Universitat Rovira i Virgili, 2013. http://hdl.handle.net/10803/365571.

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El objetivo general del trabajo presentado es investigar nuevas metodologías para la síntesis de: a) nectrisina, un inhibidor de α-glucosidasas y α-mannosidasas, b) del fragmento oligosacarídico del antibiótico AT2433-A1, un antibiótico utilizado en el tratamiento de numerosos tipos de cánceres y, c) de análogos del cidofovir o HPMPC, nucleósido acíclico que incorpora una unidad de fosfonato, y que se utiliza en el tratamiento del citomegalovirus (CMV) en pacientes con SIDA. Síntesis enantioselectiva de nectrisina Retrosintéticamente la síntesis de la nectrisina puede llevarse a cabo por ciclación del aminoaldehído 2 (R4=CHO), el cual puede proceder del alqueno trans 3 mediante una reacción de dihidroxilación estereoselectiva. La síntesis de 3 puede llevarse a cabo a partir de 4 mediante elongación de la cadena utilizando la reacción de metatesis cruzada catalizada por rutenio. Finalmente, el intermedio clave 4 procede de una aminación alílica asimétrica catalizada por Pd del monepóxido de butadieno racémico 5, reacción ya descrita por Trost. La aminación alílica asimétrica del monepóxido de butadieno racémico catalizada por Pd (η3-C3H5)PdCl/DACH-naftilo transcurrió con elevado rendimiento y enantioselectividad para dar el compuesto 4. La elongación de la cadena de 4 se realizó mediante una metatesis cruzada catalizada por el catalizador de Grubbs-Hoveyda con diferentes alquenos como acroleína, 2-vinil-1,3-dioxolano, y con acrilato de etilo. Sólo en este último caso se obtuvieron resultados relevantes del compuesto 3 (R4=COOEt) como para continuar la síntesis. La reacción de dihidroxilación estereoselectiva del alqueno trans 3 (R4=COOEt) condujo al diol deseado 2 (R4=COOEt) con buena selectividad utilizando OsO4/TMEDA. La hidrólisis del benzoato con LiOH y la ciclación in situ condujo a la lactama, a partir de la cual se siguió una secuencia sintética descrita en la bibliografía, consistente en la sililación de los grupos hidroxilo, protección del grupo amino en forma de terc-butil carbamato, reducción del carbonilo y eliminación con desprotección concomitante de los grupo sililo para dar la imina, que en nuestras manos no logró llevarse a fin debido a problemas en la última etapa de eliminación para dar la imina. Síntesis enantioselectiva de análogos de Cidofovir HPMPC La síntesis de los análogos del cidofovir se planteó siguiendo un esquema sintético similar al de la nectrisina, en el que la síntesis del intermedio 7 se llevó a cabo mediante la aminación alílica asimétrica del monoepóxido del butadieno y posterior reacción de metátesis cruzada como pasos clave. En primer lugar se realizó la aminación alílica asimétrica catalizada por Pd (η3-C3H5)PdCl/DACH-naftil del monepóxido de butadieno racémico, con adenina y citosina la cual se optimizó hasta conseguir rendimientos y excesos enantioméricos superiores al 90%. Seguidamente se optimizó la reacción de metátesis cruzada de los compuestos obtenidos (6) con un alil fosfonato convenientemente protegido, obteniendo 7 con buen rendimiento. La síntesis de los análogos de cidofovir insaturados 8 y 9 se completó tras la desprotección de todos los grupos protectores con TMSBr. La síntesis del derivado saturado 10 se realizó mediante la hydrogenación (3 bares de hidrógeno, Pd/C durante 5h) y la eliminación de los grupos protectores. Síntesis enantioselectiva del fragmento oligosacarídico del antibiótico AT2433-A1 La retrosíntesis de 18 se planteó por ciclación electrófila inducida por yodo de 15, donde X debiera ser un grupo activador del doble enlace que a su vez se pudiera comportar como grupo saliente en la subsiguiente reacción de glicosilación a partir de 15. La síntesis del intermedio 15 se planteó por diferentes procedimientos y en particular a partir del sulfato 14, el cual provendría del diol 13, que a su vez provendría de la dihidroxilación de 12. El compuesto 12 debería poder obtenerse a partir de 5 por la secuencia clásica de DYKAT y metatesis cruzada. Así, a partir del compuesto 11 (R=Boc) se realizó la metatesis cruzada con diferentes alquenos y en particular con el alil fenil tioéter. Las limitaciones se encontraron en la reacción de dihidroxilación, ya que en casi todos los casos ensayados se produjo la oxidación del azufre, lo que conduciría al cambio de la selectividad en posteriores etapas como la ciclación. Se consiguió evitar la oxidación utilizando ligandos quirales en la dihidroxilación, pero con rendimientos muy bajos no compatibles con un esquema de síntesis por etapas.
The present thesis deals with the development of methodology for the syntheses of several organic molecules that were selected by their interesting biological properties: the antibiotic AT2433-A1, the glycosidase inhibidor nectrisine and analogs of the anti-viral Cidofovir (Figure 1.1) . Although apparently structurally unrelated, they were envisaged to be synthesized through common high-efficient key steps that involve metal-catalyzed process. Enantioselective Synthesis of nectrisine We explore an enantioselective synthesis of nectrisine based on Pd-catalyzed asymmetric allylic amination, cross-metathesis and dihydroxylation as key steps. Scheme 1 shows the retrosynthesis proposed, where the key synthon is the allylamine 4 which is obtained in high enantiomeric purity by a deracemization process using Pd/DACH as a catalytic system. Cross-metathesis will allow increasing the chain length, and at the same time would provide the aldehyde functionality necessary for formation of the cyclic imine moiety in the final nectrisine. Besides, configuration of double bond resulting from cross-metathesis must be E in order to provide the correct configuration of hydroxyl groups in 2 after the dihydroxylation reaction. The stereoselectivity of this reaction will be controlled by the stereocenter in the molecule, which could be also be enhanced by chiral ligands in a matched double stereodifferentiation process. The asymmetric allylic amination from racemic butadiene monoepoxide using (η3-C3H5)PdCl/DACH-naphtyl system and t-Butyl-benzoyl-imido carboxylate as a N-nucleophile proceeded with excellent yield (98%) and enantioselectivity (97%) to obtain the chiral allylic amine synthon 4. Elongation of the chain of the key chiral allylic imide with ethyl acrylate through cross metathesis using Hoveyda-Grubbs catalyst (5 mol %), proceeded quatitatively to obtain the trans alkene intermediates 3. The installation of the syn diol moiety via dihydroxylation of the alkene proceeded with high yield and good diastereoselectivity with OsO4/TMEDA. Hydrolysis of benzoate group in 2 with LiOH and in situ cyclization led to the lactam. Whose hydroxyl functionalities were fully protected by treatment with TBSCl. Subsequent protection with di-t-butyl dicarbonate (Boc) 2O and Et3N in CH2Cl2 gave desired product in 50% yield. The increased carbonyl electrophilicity resulting from NBoc protection should facilitate the smooth reduction of the lactam, which proceeded by reaction with Super Hydride® at −78°C to give lactol. Enantioselective Synthesis of Cidofovir Analogues In this context, the retrosynthetic proposal is shown in Scheme 2. Cidofovir (HPMPC) analogues could be obtained by double bond reduction of product 7 followed by protecting group cleavage on compound 11. Compound 7 in turn can be synthesized from compound 6 via chain elongation mediated by cross-metathesis reaction. Lastly, chiral synthon 6 could be obtained by a palladium-catalyzed dynamic kinetic asymmetric transformation (DYKAT) from racemic butadiene monoepoxide (5). The asymmetric allylic amination of racemic butadiene monoepoxide with cytosine as N-nucleophile was carried out with (η3-C3H5)PdCl/DACH-naphtyl system to obtain chiral allylic cytosine in 85% yield and 72% ee. The reaction was successfully expanded to other pyrimidine and purine bases, among which adenine afforded chiral allyl adenine in 90% yield and 92% ee. Chain elongation via Ru-cross metathesis of key allylic nucleobases and diethyl allylphosphonate with second generation Grubbs catalyst (5 mol%), produced desired compounds in 92% and 90% yield, respectively. Deprotection of all protecting groups with TMSBr afforded the desired unsaturated acyclic nucleosides 8 and 9 in good yields. Hydrogenation with (H2, /Pd/C) at 3 bar rendered the saturated Cidifovir analogues 10. Approaches to the Enantioselective Synthesis of AT2433-A1 The objective of this work was to explore a new enantioselective method to obtain AT2433-A1 with special focus on the synthesis of the 2, 4-dideoxy-4-amino-xyloside moiety. The retrosynthetic proposal is shown in Scheme 5.6. The aminodeoxysugar (19) could be obtained from 16 by eletrophile-induced cyclization. A key point is the selection of group X, since it must control the regioselectivity of the cyclization to an endo-mode and eventually must behave as a leaving group in a future glycosylation reaction. Amino alcohol 16 could be prepared from allylic amine 13 by dihydroxylation, sulphate formation and elimination. Compound 13 can be synthesized from allyl amine 12 via chain elongation mediated by cross-metathesis reaction. Lastly, chiral allyl amine 12 could be obtained, similarly to the previous chapters, by a palladium-catalyzed dynamic kinetic asymmetric transformation (DYKAT) from the racemic butadiene monoepoxide 5. On the other hand, the intermediate 15 could be also obtained by addition to the Garner aldehyde (18) followed by deprotection of the protecting groups in 17. The asymmetric allylic amination from racemic butadiene monoepoxide using (η3-C3H5)PdCl/DACH-naphtyl system and imide as a nitrogen nucleophile proceeded with good yield (96%) and enantioselectivity (90%). Chain elongation of key chiral allylic amine 12 was carried out by cross metathesis with allyl phenyl sulphide with Hoveyda-Grubbs catalyst (5 mol%) to obtain the corresponding trans alkene 13 in 80% yield. The installation of the diol moiety with OsO4 was unsuccesful, due to the competitive oxidation of sulfur, preventing the completion of the synthesis.

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Adams, David J. « Enantioselective synthesis of cyclic imides ». Thesis, University of Nottingham, 2000. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.342485.

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Bromhead, Liam Joseph. « Enantioselective Synthesis of Strigolactone Analogues ». Thesis, The University of Sydney, 2016. http://hdl.handle.net/2123/16114.

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On the instigation of A/Prof C. S. P. McErlean I have investigated asymmetric approaches for the synthesis of strigolactone analogues. Strigolactones are an emergent class of phytohormone whose biological importance is only beginning to be elucidated. As our understanding of these phytohormones expands, the importance of stereochemistry on their biological action becomes increasingly apparent. As such, methodologies which allow access to strigolactones or their analogues, in a stereocontrolled fashion are of paramount importance. In the first chapter we discuss the discovery of strigolactones and the roles they play in nature. Previous approaches to the synthesis of strigolactones, as well as the development of synthetic analogues and mimics are also discussed. In chapter two, we describe our enantioselective approach for the synthesis of the key strigolactone analogue GR24. Our approach utilised a Noyori asymmetric transfer hydrogenation to install the chiral centres in a dynamic, and catalytic manner. Chapter three describes the application of our developed methodology for the synthesis of bromo-GR24 analogues. These molecules were further functionalised with a water solubilising group, or a fluorescent tag, to enable further biological studies. We also discuss a formal synthesis of the strigolactone (−)-solanacol. Finally, we discuss work undertaken at the University of Oxford, under the supervision of A/Prof Jonathan W. Burton. Here we developed synthetic approaches toward the synthesis of the inthomycin family of natural products, utilising a highly convergent strategy and environmentally benign organoboronates.

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Livres sur le sujet "Enantioselective synthesi"

Červinka, Otakar. Enantioselective reactions in organic chemistry. London : E. Horwood, 1995.

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Hodgson, David M., dir. Organolithiums in Enantioselective Synthesis. Berlin, Heidelberg : Springer Berlin Heidelberg, 2003. http://dx.doi.org/10.1007/3-540-36117-0.

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Mehta, Daxa. Enantioselective synthesis of sulphoxides. Salford : University of Salford, 1989.

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Mahrwald, Rainer. Enantioselective Organocatalyzed Reactions I : Enantioselective Oxidation, Reduction, Functionalization and Desymmetrization. Dordrecht : Springer Science+Business Media B.V., 2011.

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Baxter, Andrew Douglas. Enantioselective synthesis of aminotetralins : Novel synthetic applications of amino acids. Norwich : University of East Anglia, 1994.

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Ho, Tse-Lok. Enantioselective synthesis : Natural products from chiral terpenes. New York : Wiley, 1992.

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Eusebio, Juaristi, dir. Enantioselective synthesis of [beta]-amino acids. New York : Wiley-VCH, 1997.

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I, Dalko Peter, dir. Enantioselective organocatalysis : Reactions and experimental procedures. Weinheim : Wiley-VCH, 2007.

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Dalko, Peter I. Enantioselective organocatalysis : Reactions and experimental procedures. Weinheim : Wiley-VCH, 2007.

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Juaristi, Eusebio, et Vadim A. Soloshonok, dir. Enantioselective Synthesis of β-Amino Acids. Hoboken, NJ, USA : John Wiley & Sons, Inc., 2005. http://dx.doi.org/10.1002/0471698482.

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Plus de sources

Chapitres de livres sur le sujet "Enantioselective synthesi"

Uzir, Mohamad Hekarl. « Enantioselective Synthesis ». Dans Encyclopedia of Membranes, 700. Berlin, Heidelberg : Springer Berlin Heidelberg, 2016. http://dx.doi.org/10.1007/978-3-662-44324-8_2070.

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Uzir, Mohamad Hekarl. « Enantioselective Synthesis ». Dans Encyclopedia of Membranes, 1–2. Berlin, Heidelberg : Springer Berlin Heidelberg, 2015. http://dx.doi.org/10.1007/978-3-642-40872-4_2070-1.

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Normant, Jean F. « Enantioselective Carbolithiations ». Dans Organolithiums in Enantioselective Synthesis, 287–310. Berlin, Heidelberg : Springer Berlin Heidelberg, 2003. http://dx.doi.org/10.1007/3-540-36117-0_9.

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Marqués-López, Eugenia, et Raquel P. Herrera. « Organocatalysis in Total Synthesis ». Dans Comprehensive Enantioselective Organocatalysis, 1359–83. Weinheim, Germany : Wiley-VCH Verlag GmbH & Co. KGaA, 2013. http://dx.doi.org/10.1002/9783527658862.ch44.

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Wang, Qian, Jieping Zhu et Mei-Xiang Wang. « Enantioselective Passerini Reaction ». Dans Asymmetric Synthesis II, 95–101. Weinheim, Germany : Wiley-VCH Verlag GmbH & Co. KGaA, 2013. http://dx.doi.org/10.1002/9783527652235.ch13.

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Hodgson, David M., et Matthew A. H. Stent. « Overview of Organolithium-Ligand Combinations and Lithium Amides for Enantioselective Processes ». Dans Organolithiums in Enantioselective Synthesis, 1–20. Berlin, Heidelberg : Springer Berlin Heidelberg, 2003. http://dx.doi.org/10.1007/3-540-36117-0_1.

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Goldfuss, Bernd. « Enantioselective Addition of Organolithiums to C=O Groups and Ethers ». Dans Organolithiums in Enantioselective Synthesis, 21–36. Berlin, Heidelberg : Springer Berlin Heidelberg, 2003. http://dx.doi.org/10.1007/3-540-36117-0_2.

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Iguchi, Mayu, Ken-ichi Yamada et Kiyoshi Tomioka. « Enantioselective Conjugate Addition and 1,2-Addition to C=N of Organolithium Reagents ». Dans Organolithiums in Enantioselective Synthesis, 37–59. Berlin, Heidelberg : Springer Berlin Heidelberg, 2003. http://dx.doi.org/10.1007/3-540-36117-0_3.

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Hoppe, Dieter, Felix Marr et Markus Brüggemann. « Enantioselective Synthesis by Lithiation Adjacent to Oxygen and Electrophile Incorporation ». Dans Organolithiums in Enantioselective Synthesis, 61–138. Berlin, Heidelberg : Springer Berlin Heidelberg, 2003. http://dx.doi.org/10.1007/3-540-36117-0_4.

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Beak, Peter, Timothy A. Johnson, Dwight D. Kim et Sung H. Lim. « Enantioselective Synthesis by Lithiation Adjacent to Nitrogen and Electrophile Incorporation ». Dans Organolithiums in Enantioselective Synthesis, 139–76. Berlin, Heidelberg : Springer Berlin Heidelberg, 2003. http://dx.doi.org/10.1007/3-540-36117-0_5.

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Actes de conférences sur le sujet "Enantioselective synthesi"

Bagnoli, Luana, Marcello Tiecco, Lorenzo Testaferri, Catalina Scarponi, Andrea Temperini, Francesca Marini et Claudio Santi. « Selenium Promoted Enantioselective Synthesis of Spiroketals ». Dans The 9th International Electronic Conference on Synthetic Organic Chemistry. Basel, Switzerland : MDPI, 2005. http://dx.doi.org/10.3390/ecsoc-9-01519.

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Carrillo Fernández, Luisa, Jose Luis Vicario, Iker Riaño, Estibaliz Diaz, Efraim Reyes Martín et Uxue Uria. « Enantioselective Synthesis of Chiral Proline Derivatives ». Dans MOL2NET 2016, International Conference on Multidisciplinary Sciences, 2nd edition. Basel, Switzerland : MDPI, 2016. http://dx.doi.org/10.3390/mol2net-02-h004.

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Eames, Jason, Ewan Boyd, Alastair Hay, Ray Jones, Rachel Stenson et Michael Suggate. « Enantioselective Protonation of Prostereogenic Enol Equivalents ». Dans The 10th International Electronic Conference on Synthetic Organic Chemistry. Basel, Switzerland : MDPI, 2006. http://dx.doi.org/10.3390/ecsoc-10-01388.

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Correia, Carlos Roque Duarte. « Enantioselective Heck Reactions with Aryldiazonium Salts. Challenges and Synthetic Opportunities ». Dans 15th Brazilian Meeting on Organic Synthesis. São Paulo : Editora Edgard Blücher, 2013. http://dx.doi.org/10.5151/chempro-15bmos-speech15.

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Barabás, Béla, Luciano Caglioti, Francesco Faglioni, Nicola Florini, Paolo Lazzeretti, Marco Maioli, Károly Micskei et al. « On the Traces of Absolute Enantioselective Synthesis ». Dans COMPUTATIONAL METHODS IN SCIENCE AND ENGINEERING : Theory and Computation : Old Problems and New Challenges. Lectures Presented at the International Conference on Computational Methods in Science and Engineering 2007 (ICCMSE 2007) : VOLUME 1. AIP, 2007. http://dx.doi.org/10.1063/1.2835949.

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Silva, Tiago Lima da, et Paulo Henrique Schneider. « Multicomponent Synthesis of Bifunctional Thiourea Organocatalysts for the Enantioselective Aldol Reaction ». Dans 14th Brazilian Meeting on Organic Synthesis. São Paulo : Editora Edgard Blücher, 2013. http://dx.doi.org/10.5151/chempro-14bmos-r0012-1.

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Soares, Liliana A., Helena D. de Salles et Paulo H. Schneider. « Highly enantioselective arylation of aromatic aldehydes, promoted by chiral phosphinite ligands ». Dans 14th Brazilian Meeting on Organic Synthesis. São Paulo : Editora Edgard Blücher, 2013. http://dx.doi.org/10.5151/chempro-14bmos-r0018-1.

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Wosch, Celso L., Francisco A. Marques, Gustavo Frensch, Ricardo Labes, Beatriz Helena L. N. Sales Maia, Cesar A. Lenz et Palimecio G. Guerrero Jr. « Chiral -Hydroxyalkyloxazolines as Ligands in the Enantioselective Addition of Diethylzinc to Aldehydes ». Dans 14th Brazilian Meeting on Organic Synthesis. São Paulo : Editora Edgard Blücher, 2013. http://dx.doi.org/10.5151/chempro-14bmos-r0251-1.

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Manoel*, Evelin A., Maria Alice Z. Coelho, Rodrigo O. M. A. de Souza, Alessandro B. C. Simas et Denise M. G. Freire. « Enantioselective catalysis from Pseudomonas cepacia on the kinetic resolution by different reactors ». Dans 15th Brazilian Meeting on Organic Synthesis. São Paulo : Editora Edgard Blücher, 2013. http://dx.doi.org/10.5151/chempro-15bmos-bmos2013_201383123328.

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Sakae, George H., Leandro M. Takata, Antonio S. Paulino, Reinaldo C. Bazito, Rafael F. Cassaro, Cleverson Princival et Alcindo A. Dos Santos. « A high enantioselective Proline-based helical polymer catalyst for aldol type reaction ». Dans 15th Brazilian Meeting on Organic Synthesis. São Paulo : Editora Edgard Blücher, 2013. http://dx.doi.org/10.5151/chempro-15bmos-bmos2013_2013912163332.

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