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 - 2012

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Stereoselectivity
Carbamates
Sulfonamides
Isomers
selectivity
preparation
Substrates
chelates
elimination
isomers

Keywords

  • enamides
  • glycidyl sulfonamides
  • carbamates

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, 2012, p. 509-511.

Research output: Contribution to journalArticle

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T1 - E- and Z-Stereoselectivity in the preparation of enamides from glycidyl sulfonamides and carbamates

AU - Brown, Jack A

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

PY - 2012

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AB - 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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KW - glycidyl sulfonamides

KW - carbamates

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U2 - 10.1039/c1ob06569f

DO - 10.1039/c1ob06569f

M3 - Article

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EP - 511

JO - Organic and Biomolecular Chemistry

T2 - Organic and Biomolecular Chemistry

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