Issue 3, 2012
From the journal:

Organic & Biomolecular Chemistry

E- and Z-Stereoselectivity in the preparation of enamides from glycidyl sulfonamides and carbamates†

Jack A. Brown,‡ab   Vijay Chudasama,§a   Melvyn E. Giles,a   Duncan M. Gill,*a   Philip S. Keegan,a   William J. Kerr,b   Rachel H. Munday,a   Karen Griffin||a  and  Andrew Wattsa  

* Corresponding authors

a Pharmaceutical Development, AstraZeneca R&D Charnwood, Bakewell Road, Loughborough, UK

b Department of Pure and Applied Chemistry, University of Strathclyde, 295 Cathedral Street, Glasgow, UK

Abstract

Treatment of glycidyl sulfonamides with LDA delivers the corresponding enesulfonamide with good selectivity for the E-isomer, whereas the corresponding carbamates exhibit selectivity for the Z-enecarbamate. An E1cB elimination mechanism proceeding from a substrate–base chelate complex is advanced as rationalisation of the latter set of Z-selective outcomes.

Graphical abstract: E- and Z-Stereoselectivity in the preparation of enamides from glycidyl sulfonamides and carbamates

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Article information

DOI
https://doi.org/10.1039/C1OB06569F
Article type
Communication
Submitted
13 Sep 2011
Accepted
10 Nov 2011
First published
16 Nov 2011

Org. Biomol. Chem., 2012,10, 509-511

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E- and Z-Stereoselectivity in the preparation of enamides from glycidyl sulfonamides and carbamates

J. A. Brown, V. Chudasama, M. E. Giles, D. M. Gill, P. S. Keegan, W. J. Kerr, R. H. Munday, K. Griffin and A. Watts, Org. Biomol. Chem., 2012, 10, 509 DOI: 10.1039/C1OB06569F

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