Formalizing the mechanism of the allylic substitution reaction (SN'): Application to the highly enantio- and diastereo-selective syntheses of 1-phenyl-2-vinylcyclopentanes

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Résumé

We report efficient stereoselective and high yielding syntheses of each of the four enantiomers of phenylcyclopentanes bearing a quaternary center and a E-propenyl chain on the adjacent carbon that involves intramolecular allylic substitution reactions. In complement to its synthetic value, this process models the SN' reaction and allows prediction of its stereochemical outcome.

langue originaleAnglais
Pages (de - à)308-333
Nombre de pages26
journalARKIVOC
Volume2018
Numéro de publication5
Les DOIs
Etat de la publicationPublié - 7 juil. 2018

Financement

The work presented in this paper was initiated in 2004 by Francois Adam (FA) assistant and enrolled as a PhD student, then carried out in 2007 by Hélène Vanderhauwaer (HV) a PhD student supported by the FRIA Belgium (Laboratoire de Chimie Organique de Synthèse, Facultés N.D de la Paix, Namur). Both of them decided to stop their work for personal reasons. Their fragmentary results have been consigned in their progress reports (a) January-July 2005 and (b) January-July 2007 respectively. All the results reported here, except those involving the transformation of 4cE to 11 and 4a (FA, research report 2005) have been carried out by Dr Adrian Kremer in the laboratory of Prof. D. Bonifazi. The Authors thanks Prof. Davide Bonifazi for strongly supporting this work and Prof. Guillaume Berionni for helpful discussions.

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