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

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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.
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

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    Brown, J. A., Chudasama, V., Giles, M. E., Gill, D. M., Keegan, P. S., Kerr, W. J., Munday, R. H., Griffin, K., & Watts, A. (2012). E- and Z-Stereoselectivity in the preparation of enamides from glycidyl sulfonamides and carbamates. Organic and Biomolecular Chemistry, 10(3), 509-511. https://doi.org/10.1039/c1ob06569f