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

Pure And Applied Chemistry

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3 Citations (Scopus)

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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 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 - 2012

Keywords

enamides
glycidyl sulfonamides
carbamates

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Gill Kerr Glycidyl Carbamate OBC PublishedFinal published version, 205 KB

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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.",

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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

Y1 - 2012

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.

KW - enamides

KW - glycidyl sulfonamides

KW - carbamates

UR - https://www.scopus.com/pages/publications/84055178603

U2 - 10.1039/c1ob06569f

DO - 10.1039/c1ob06569f

M3 - Article

SN - 1477-0520

VL - 10

SP - 509

EP - 511

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 3

ER -

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

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Keywords

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