Issue 2, 2013
From the journal:

Chemical Science

Multifaceted interception of 2-chloro-2-oxoacetic anhydrides: a catalytic asymmetric synthesis of β-lactams†

Li Huang,a   Wenjun Zhao,a   Richard J. Staplesa  and  William D. Wulff*a  

* Corresponding authors

a Department of Chemistry, Michigan State University, East Lansing, MI, USA
E-mail: wulff@chemistry.msu.edu
Fax: +1 517-353-1793
Tel: +1 517-355-9715

Abstract

Aziridine-2-carboxylic acids will react with oxalyl chloride to give morpholin-2,3,5-trionones, cyclic N-carboxyanhydrides or β-lactams depending on the nature of the substituent at the 3-position. All substrates can be diverted to β-lactams upon treatment with a Vilsmeier reagent. The three to four membered ring expansion is stereospecific and proceeds with high yields and diastereoselection. This method provides for an asymmetric synthesis of β-lactams from simple aldehydes via a multi-component catalytic asymmetric aziridination reaction.

Graphical abstract: Multifaceted interception of 2-chloro-2-oxoacetic anhydrides: a catalytic asymmetric synthesis of β-lactams

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Article information

DOI
https://doi.org/10.1039/C2SC21240D
Article type
Edge Article
Submitted
12 Aug 2012
Accepted
08 Oct 2012
First published
08 Nov 2012

Chem. Sci., 2013,4, 622-628

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Multifaceted interception of 2-chloro-2-oxoacetic anhydrides: a catalytic asymmetric synthesis of β-lactams

L. Huang, W. Zhao, R. J. Staples and W. D. Wulff, Chem. Sci., 2013, 4, 622 DOI: 10.1039/C2SC21240D

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