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 journalArticlepeer-review

2 Citations (Scopus)
137 Downloads (Pure)

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 - 2012

Keywords

  • enamides
  • glycidyl sulfonamides
  • carbamates

Fingerprint

Dive into the research topics of 'E- and Z-Stereoselectivity in the preparation of enamides from glycidyl sulfonamides and carbamates'. Together they form a unique fingerprint.

Cite this