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Organocatalytic enantioselective allylic alkylation of α-aryl γ-lactones: an approach to densely functionalized quaternary stereocentres

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Abstract

The asymmetric allylic alkylation (AAA) of α-aryl γ-lactones involving the activation of Morita–Baylis–Hillman (MBH) carbonates by an original chiral Lewis base is reported. A wide range of γ-lactones bearing a quaternary stereocentre was thus obtained in both high yields and high enantiomeric ratios. The direct alkylation by MBH alcohol using in situ activation has been also established. Additionally synthetically useful functional transformations of groups surrounding the quaternary stereocentre have been performed.

Graphical abstract: Organocatalytic enantioselective allylic alkylation of α-aryl γ-lactones: an approach to densely functionalized quaternary stereocentres

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Supplementary files

Article information


Submitted
19 Mar 2020
Accepted
05 May 2020
First published
14 May 2020

Chem. Commun., 2020, Advance Article
Article type
Communication

Organocatalytic enantioselective allylic alkylation of α-aryl γ-lactones: an approach to densely functionalized quaternary stereocentres

M. Mando, F. Grellepois and E. Riguet, Chem. Commun., 2020, Advance Article , DOI: 10.1039/D0CC02058C

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