Dramatic influence of ester steric hindrance on the diastereoselectivity of a Michael addition towards the synthesis of the ABC tricycle of hexacyclinic acid

Audic, A., Oriez, R. and Prunet, J. (2021) Dramatic influence of ester steric hindrance on the diastereoselectivity of a Michael addition towards the synthesis of the ABC tricycle of hexacyclinic acid. Tetrahedron, 79, 131843. (doi: 10.1016/j.tet.2020.131843)

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Abstract

During our studies toward the synthesis of the ABC ring system of hexacyclinic acid, we observed an unexpected influence of the steric bulk of the ester group of the Michael acceptor in a key conjugate addition. We propose an eight-membered ring transition state to explain the formation of the undesired diastereomer in the case of unhindered esters.

Item Type:Articles
Status:Published
Refereed:Yes
Glasgow Author(s) Enlighten ID:Prunet, Dr Joelle and Audic, Alexandre Baptiste Robert
Authors: Audic, A., Oriez, R., and Prunet, J.
College/School:College of Science and Engineering > School of Chemistry
Journal Name:Tetrahedron
Publisher:Elsevier
ISSN:0040-4020
ISSN (Online):1464-5416
Published Online:04 December 2020
Copyright Holders:Copyright © 2020 Elsevier Ltd.
First Published:First published in Tetrahedron 79: 131843
Publisher Policy:Reproduced in accordance with the publisher copyright policy

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Project CodeAward NoProject NamePrincipal InvestigatorFunder's NameFunder RefLead Dept
190490Engineering and Physical Sciences Doctoral Training Grant 2012-16Mary Beth KneafseyEngineering and Physical Sciences Research Council (EPSRC)EP/K503058/1Research and Innovation Services