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

Jack A. Brown, Vijay Chudasama, Melvyn E. Giles, Duncan M. Gill, Philip S. Keegan, William J. Kerr, Rachel H. Munday, Karen Griffin, Andrew Watts

Research output: Contribution to journalArticle

2 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)509-511
Number of pages3
JournalOrganic and Biomolecular Chemistry
Volume10
Issue number3
Early online date16 Nov 2011
DOIs
Publication statusPublished - 21 Jan 2012
Externally publishedYes

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