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You searched for subject:( vinylcyclopropanes). Showing records 1 – 3 of 3 total matches.

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1. Laugeois, Maxime. Réactions de cycloadditions stéréosélectives originales reposant sur l'utilisation de vinylcyclopropanes électro-appauvris et la catalyse au palladium(0) : Original stereoselective cycloaddition reactions based on the use of electron-poor vinylcyclopropanes and palladium(0) calaysis.

Degree: Docteur es, Chimie organique, 2017, Université Pierre et Marie Curie – Paris VI

Ce manuscrit présente le développement de nouvelles réactions de cycloaddition [3+2] palladocatalysées entre des vinylcyclopropanes électro-appauvris et diverses espèces dipolarophiles. La première partie de ces travaux a porté sur la désaromatisation de composés nitroaromatiques tels que les 3-nitroindoles ou les 2-nitrobenzofuranes par le biais d'un procédé de cycloaddition impliquant les vinylcyclopropanes. Une seconde méthodologie de cycloaddition [3+2] énantiosélective entre des aldéhydes ?,?-insaturés et des vinylcyclopropanes a été développée. En tirant parti du concept de catalyse synergique métallo-organique, divers cyclopentanes hautement fonctionnalisés ont été obtenus, avec notamment des énantiosélectivités très élevées. Dans une troisième partie de ces travaux, l'extension de cette méthodologie à la synthèse de composés hétérocycliques a été étudiée ; une première approche impliquant la formation in situ de dipôles-1,3 et -1,4 azotés n'ayant pas abouti à la réactivité désirée, nous avons alors développé une méthodologie de cycloaddition de vinylcyclopropanes et d'imines électro-déficientes par catalyse au palladium(0) menant à des dérivés de pyrrolidine.

This manuscript presents the development of novel palladium-catalysed [3+2] cycloaddition reactions between vinylcyclopropanes and various dipolarophiles. The first part of this work focused on the dearomatization of nitroaromatic compounds such as 3-nitroindoles and 2-nitrobenzofurans through a cycloaddition process with vinylcyclopropanes. In a second time, an enantioselective [3+2] cycloaddition of vinylcyclopropanes with α,β-unsaturated aldehydes under a synergistic metal-organocatalytic activation manifold was developed, leading to highly substituted cyclopentane scaffolds with very high enantioselectivity. In a third part of this work, the extension of this methodology towards the synthesis of heterocyclic compounds was investigated. A first approach dealing with the in situ generation of nitrogen-containing 1,3- and 1,4-dipoles did not lead to the desired reactivity, which prompted us to develop a palladium(0)-catalysed cycloaddition of vinylcyclopropanes and electron-deficient imines to synthesize pyrrolidine derivatives.

Advisors/Committee Members: Vidal, Virginie (thesis director), Vitale, Maxime (thesis director), Michelet, Véronique (thesis director).

Subjects/Keywords: Cycloaddition [3+2]; Palladium; Vinylcyclopropanes; Désaromatisation; Métallo-organocatalyse; Catalyse asymétrique; Palladium; Asymmetric catalysis; Vinylcyclopropanes; 547

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APA · Chicago · MLA · Vancouver · CSE | Export to Zotero / EndNote / Reference Manager

APA (6th Edition):

Laugeois, M. (2017). Réactions de cycloadditions stéréosélectives originales reposant sur l'utilisation de vinylcyclopropanes électro-appauvris et la catalyse au palladium(0) : Original stereoselective cycloaddition reactions based on the use of electron-poor vinylcyclopropanes and palladium(0) calaysis. (Doctoral Dissertation). Université Pierre et Marie Curie – Paris VI. Retrieved from http://www.theses.fr/2017PA066353

Chicago Manual of Style (16th Edition):

Laugeois, Maxime. “Réactions de cycloadditions stéréosélectives originales reposant sur l'utilisation de vinylcyclopropanes électro-appauvris et la catalyse au palladium(0) : Original stereoselective cycloaddition reactions based on the use of electron-poor vinylcyclopropanes and palladium(0) calaysis.” 2017. Doctoral Dissertation, Université Pierre et Marie Curie – Paris VI. Accessed November 12, 2019. http://www.theses.fr/2017PA066353.

MLA Handbook (7th Edition):

Laugeois, Maxime. “Réactions de cycloadditions stéréosélectives originales reposant sur l'utilisation de vinylcyclopropanes électro-appauvris et la catalyse au palladium(0) : Original stereoselective cycloaddition reactions based on the use of electron-poor vinylcyclopropanes and palladium(0) calaysis.” 2017. Web. 12 Nov 2019.

Vancouver:

Laugeois M. Réactions de cycloadditions stéréosélectives originales reposant sur l'utilisation de vinylcyclopropanes électro-appauvris et la catalyse au palladium(0) : Original stereoselective cycloaddition reactions based on the use of electron-poor vinylcyclopropanes and palladium(0) calaysis. [Internet] [Doctoral dissertation]. Université Pierre et Marie Curie – Paris VI; 2017. [cited 2019 Nov 12]. Available from: http://www.theses.fr/2017PA066353.

Council of Science Editors:

Laugeois M. Réactions de cycloadditions stéréosélectives originales reposant sur l'utilisation de vinylcyclopropanes électro-appauvris et la catalyse au palladium(0) : Original stereoselective cycloaddition reactions based on the use of electron-poor vinylcyclopropanes and palladium(0) calaysis. [Doctoral Dissertation]. Université Pierre et Marie Curie – Paris VI; 2017. Available from: http://www.theses.fr/2017PA066353


Indian Institute of Science

2. Ganesh, V. Studies On the Ring-Opening Reaftions Of Vinylcyclopropanes, Vinylcyclobutanes And Other Snmall-Ring Systems.

Degree: 2012, Indian Institute of Science

The thesis entitled “Studies on the Ring-opening Reactions of Vinylcyclopropanes, Vinylcyclobutanes, and other Small-ring Systems” is divided into four chapters. Chapter 1: Part A: Bromenium Catalyzed Tandem Ring-opening/Cyclization of Vinylcyclopropanes and Vinylcyclobutanes: A [3+2+1]/[4+2+1] Cascade for the Synthesis of Chiral Amidines. In this part of the Chapter, we discuss our serendipitous results in the reaction of vinylcyclopropanes (VCPs), like Δ2-carene under Sharpless aziridination conditions using chloramine-T and phenyltrimethylammonium tribromide (PTAB) as catalyst in acetonitrile. The reaction follows a [3+2+1] cascade pathway involving acetonitrile (Ritter-type reaction) to give chiral bicyclic amidines in very good yield. The reaction was found to be tolerant to hydroxyl- and keto-functionalities. . existence of a tight-carbocation intermediate. Our attempts to access bridged bicyclic amidines from vinylcyclobutanes like α-pinene resulted in the formation of bicyclo[4.3.1]pyrimidines successfully in moderate yields. Partial racemization of the product was observed and this observation was rationalized through competing cyclization pathways. Vinylcyclopropanes and Vinylcyclobutanes towards the Synthesis of Chiral Amidines. In this part of the chapter, we discuss our computational results obtained from modeling the reaction pathway in gas-phase and solvent dielectrics (acetonitrile). Initially, we modeled the ring-opening process, to visualize the geometrical features and the orbital interactions present in the tight-carbocation intermediate. We also modeled the competing cyclization pathways to justify the racemization observed in the case of α-pinene. Our calculations show that, the free energy of activation for the allylic substitution and the direct substitution pathways are nearly equal. Thus, the formation of both the enantiomers is feasible kinetically. the proposed cascade pathway. Chapter 2: Electrophile-Induced Indirect Activation of C-C Bond of Vinylcyclopropanes: A Masked Donor-Acceptor Strategy for the Synthesis of Z-Alkylidenetetrahydrofurans. In Chapter 2, we discuss the results of introducing VCPs as masked donor-acceptor systems under electrophilic conditions. Our aim was to activate the VCPs with in situ generated bromine electrophile to give a tight-carbocation as discussed in Chapter 1. Further, the tight-carbocation can be used to access novel heterocycles. formation of Z-alkylidienetetrahydrofurans with high stereoselectivity across the exocyclic double bond. An interesting reactivity of benzofuran derived VCPs was observed, where the ring-opening occurred concurrently adjacent to the heteroatom and at the benzylic position to give both cis- and trans-furofuran. methyl group on VCP as a chiral marker. Under our standard reaction conditions, cyclization resulted in the retention of configuration at the phenyl center. The retention of configuration results through a directed attack of hydroxyl group on the tight-carbocation. … Advisors/Committee Members: Chandrasekaran, S.

Subjects/Keywords: Vinylcyclopropanes - Ring-Opening; Vinylcyclobutanes - Ring-Opening; Chiral Amidines - Synthesis; Vinylcyclopropane Rearrangement; Small-Ring Systems; Vinylcyclopropanes- Cyclization; Vinylcyclobutanes - Cyclization; Vinylcyclopropane Reactivity; Organic Chemistry

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APA · Chicago · MLA · Vancouver · CSE | Export to Zotero / EndNote / Reference Manager

APA (6th Edition):

Ganesh, V. (2012). Studies On the Ring-Opening Reaftions Of Vinylcyclopropanes, Vinylcyclobutanes And Other Snmall-Ring Systems. (Thesis). Indian Institute of Science. Retrieved from http://hdl.handle.net/2005/3237

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

Chicago Manual of Style (16th Edition):

Ganesh, V. “Studies On the Ring-Opening Reaftions Of Vinylcyclopropanes, Vinylcyclobutanes And Other Snmall-Ring Systems.” 2012. Thesis, Indian Institute of Science. Accessed November 12, 2019. http://hdl.handle.net/2005/3237.

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

MLA Handbook (7th Edition):

Ganesh, V. “Studies On the Ring-Opening Reaftions Of Vinylcyclopropanes, Vinylcyclobutanes And Other Snmall-Ring Systems.” 2012. Web. 12 Nov 2019.

Vancouver:

Ganesh V. Studies On the Ring-Opening Reaftions Of Vinylcyclopropanes, Vinylcyclobutanes And Other Snmall-Ring Systems. [Internet] [Thesis]. Indian Institute of Science; 2012. [cited 2019 Nov 12]. Available from: http://hdl.handle.net/2005/3237.

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

Council of Science Editors:

Ganesh V. Studies On the Ring-Opening Reaftions Of Vinylcyclopropanes, Vinylcyclobutanes And Other Snmall-Ring Systems. [Thesis]. Indian Institute of Science; 2012. Available from: http://hdl.handle.net/2005/3237

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

3. Stelzer, Frank. Totalsynthese von Turrianen - Anwendung und Vergleich von RCM und RCAM.

Degree: 2002, Universität Dortmund

Subjects/Keywords: allyl cation; Allylkation; atom economy; Atomökonomie; cationic reaction pathway; Deuterium labelling; Deuterium-Markierung; DNA-cleaving activity; DNA-spaltende Aktivität; Enine; Enynes; (e/z)-selectivity; (E/Z)-Selektivität; highly substituted biaryl moiety; Hochsubstituierte Biaryleinheit; Kationischer Reaktionsweg; LEWIS acids; LEWIS-Säuren; macrocyclization; Makrocyclisierung; microwave heating; Mikrowellenbestrahlung; natural product synthesis; Naturstoffsynthese; n-heterocyclic carbenes; N-Heterocyclische Carbene; O-C Allyltransfer; O-C allyltransfer; Oxazoline; oxazolines; Platin-katalysierte Cycloisomerisierungen; platinum-catalyzed cycloisomerizations; ring closing alkyne metathesis; ring closing olefin metathesis; Ringschlußalkinmetathese; Ringschluß-olefinmetathese; ruthenium-catalyzed enyne metathesis; Ruthenium-katalysierte Enin-Metathese; turriane; turrianes; vinylcyclopropane; vinylcyclopropanes; 540

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APA · Chicago · MLA · Vancouver · CSE | Export to Zotero / EndNote / Reference Manager

APA (6th Edition):

Stelzer, F. (2002). Totalsynthese von Turrianen - Anwendung und Vergleich von RCM und RCAM. (Thesis). Universität Dortmund. Retrieved from http://hdl.handle.net/2003/2486

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

Chicago Manual of Style (16th Edition):

Stelzer, Frank. “Totalsynthese von Turrianen - Anwendung und Vergleich von RCM und RCAM.” 2002. Thesis, Universität Dortmund. Accessed November 12, 2019. http://hdl.handle.net/2003/2486.

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

MLA Handbook (7th Edition):

Stelzer, Frank. “Totalsynthese von Turrianen - Anwendung und Vergleich von RCM und RCAM.” 2002. Web. 12 Nov 2019.

Vancouver:

Stelzer F. Totalsynthese von Turrianen - Anwendung und Vergleich von RCM und RCAM. [Internet] [Thesis]. Universität Dortmund; 2002. [cited 2019 Nov 12]. Available from: http://hdl.handle.net/2003/2486.

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

Council of Science Editors:

Stelzer F. Totalsynthese von Turrianen - Anwendung und Vergleich von RCM und RCAM. [Thesis]. Universität Dortmund; 2002. Available from: http://hdl.handle.net/2003/2486

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

.