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

doi:10.1039/c1ob06569f

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 journal › Article › peer-review

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 language	English
Pages (from-to)	509-511
Number of pages	3
Journal	Organic and Biomolecular Chemistry
Volume	10
Issue number	3
Early online date	16 Nov 2011
DOIs	https://doi.org/10.1039/c1ob06569f
Publication status	Published - 21 Jan 2012
Externally published	Yes

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title = "E- and Z-Stereoselectivity in the preparation of enamides from glycidyl sulfonamides and carbamates",

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.",

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

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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 - 2012/1/21

Y1 - 2012/1/21

N2 - 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.

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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U2 - 10.1039/c1ob06569f

DO - 10.1039/c1ob06569f

M3 - Article

C2 - 22124587

AN - SCOPUS:84055178603

VL - 10

SP - 509

EP - 511

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

SN - 1477-0520

IS - 3

ER -

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

Abstract

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