Issue 16, 2001
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Trapping highly reactive dipolarophiles. Exploiting the mechanism associated with the azomethine ylide strategy for β-lactam synthesis

Giles A. Brown,a   Kirsty M. Anderson,a   Jonathan M. Large,a   Denis Planchenault,a   Dominique Urban,a   Neil J. Halesb  and  Timothy Gallagher*a  

* Corresponding authors

a School of Chemistry, University of Bristol, Bristol, UK

b AstraZeneca, Mereside, Alderley Park, Macclesfield, UK

Abstract

Highly reactive thioaldehydes 7, which are generated transiently by thermolysis of thiosulfinates 6, are trapped using azomethine ylide (derived from the β-lactam based oxazolidinone 1) to give 2-substituted penams 8. Diethyl thioxomalonate 10 and the selenoxo analogue 13, both of which are generated transiently via a retro Diels–Alder reaction, undergo 1,3-dipolar cycloaddition reactions with 1 to give the isomeric penam 11a and isopenam 11b, and the 2,2-disubstituted selenapenam 14 respectively.

Graphical abstract: Trapping highly reactive dipolarophiles. Exploiting the mechanism associated with the azomethine ylide strategy for β-lactam synthesis

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Article information

DOI
https://doi.org/10.1039/B103271M
Article type
Paper
Submitted
11 Apr 2001
Accepted
27 Jun 2001
First published
27 Jul 2001

J. Chem. Soc., Perkin Trans. 1, 2001, 1897-1900

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Trapping highly reactive dipolarophiles. Exploiting the mechanism associated with the azomethine ylide strategy for β-lactam synthesis

G. A. Brown, K. M. Anderson, J. M. Large, D. Planchenault, D. Urban, N. J. Hales and T. Gallagher, J. Chem. Soc., Perkin Trans. 1, 2001, 1897 DOI: 10.1039/B103271M

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