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

Brown, Jack A., Chudasama, Vijay, Giles, Melvyn E., Gill, Duncan M., Keegan, Phillip S., Kerr, William J., Munday, Rachel, Griffin, Karen and Watts, Andrew (2012) E- and Z-Stereoselectivity in the preparation of enamides from glycidyl sulfonamides and carbamates. Organic & Biomolecular Chemistry, 10 (3). pp. 509-511. ISSN 1477-0520
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.

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Article
Depositing User:
Duncan Gill
Date Deposited:
01 Jun 2012 09:03
Revision:
29
Last Modified:
28 Aug 2021 20:53
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