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Issue 3, 2012
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E- and Z-Stereoselectivity in the preparation of enamides from glycidyl sulfonamides and carbamates

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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


Submitted
13 Sep 2011
Accepted
10 Nov 2011
First published
16 Nov 2011

Org. Biomol. Chem., 2012,10, 509-511
Article type
Communication

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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