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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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Publication details

The article was received on 13 Sep 2011, accepted on 10 Nov 2011 and first published on 16 Nov 2011


Article type: Communication
DOI: 10.1039/C1OB06569F
Citation: 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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