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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 27, 1997 - Issue 21
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Original Articles

An Investigation of the N-Arylsulfonylation of 2-Azetidinones

Robert M. Adlington The Dyson Perrins Laboratory, University of Oxford, South Parks Road, Oxford, OX1 3QY, UK
,
Jack E. Baldwin The Dyson Perrins Laboratory, University of Oxford, South Parks Road, Oxford, OX1 3QY, UK
,
William MC Coull The Dyson Perrins Laboratory, University of Oxford, South Parks Road, Oxford, OX1 3QY, UK
,
Gareth J. Pritchard The Dyson Perrins Laboratory, University of Oxford, South Parks Road, Oxford, OX1 3QY, UK
,
Christopher J. Schofield The Dyson Perrins Laboratory, University of Oxford, South Parks Road, Oxford, OX1 3QY, UK
&
Nicholas J. Westwood The Dyson Perrins Laboratory, University of Oxford, South Parks Road, Oxford, OX1 3QY, UK
Pages 3803-3813 | Received 15 Apr 1997, Published online: 22 Aug 2006
 
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Abstract

N-Arylsulfonylation of 2-azetidinones can lead to the diastereoselective formation of oligomerization products. However, a simple increase of arylsulfonyl chloride concentration minimized oligomerization and allowed preparation of 1-arylsulfonyl-2-azetidinones in good yield.

Notes

Synthetic procedures for the preparation of the 2-azetidinones substrates will be detailed in future publications.

The arylsulfonyl chloride was added in one portion dissolved in the minimum amount of tetrahydrofuran.

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