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.

LanguageEnglish
Pages509-511
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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Stereoselectivity
Carbamates
Sulfonamides
Isomers
selectivity
preparation
Substrates
chelates
elimination
isomers

Cite this

Brown, Jack A. ; Chudasama, Vijay ; Giles, Melvyn E. ; Gill, Duncan M. ; Keegan, Philip S. ; Kerr, William J. ; Munday, Rachel H. ; Griffin, Karen ; Watts, Andrew. / E- and Z-Stereoselectivity in the preparation of enamides from glycidyl sulfonamides and carbamates. In: Organic and Biomolecular Chemistry. 2012 ; Vol. 10, No. 3. pp. 509-511.
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Brown, JA, Chudasama, V, Giles, ME, Gill, DM, Keegan, PS, Kerr, WJ, Munday, RH, Griffin, K & Watts, A 2012, 'E- and Z-Stereoselectivity in the preparation of enamides from glycidyl sulfonamides and carbamates', Organic and Biomolecular Chemistry, vol. 10, no. 3, pp. 509-511. https://doi.org/10.1039/c1ob06569f

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, Philip S.; Kerr, William J.; Munday, Rachel H.; Griffin, Karen; Watts, Andrew.

In: Organic and Biomolecular Chemistry, Vol. 10, No. 3, 21.01.2012, p. 509-511.

Research output: Contribution to journalArticle

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AU - Chudasama, Vijay

AU - Giles, Melvyn E.

AU - Gill, Duncan M.

AU - Keegan, Philip S.

AU - Kerr, William J.

AU - Munday, Rachel H.

AU - Griffin, Karen

AU - Watts, Andrew

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