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 |
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Status: | Published |
Refereed: | Yes |
Glasgow Author(s) Enlighten ID: | Audic, Alexandre Baptiste Robert and Prunet, Dr Joelle |
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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