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Synthesis 2009(11): 1923-1932  
DOI: 10.1055/s-0029-1216799
FEATUREARTICLE
© Georg Thieme Verlag Stuttgart ˙ New York

Terminal Aziridines by Addition of Grignard Reagents or Organoceriums to an (α-Chloro)sulfinylimine

David M. Hodgson*a, Johannes Kloesgesa, Brian Evansb
a Department of Chemistry, Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford OX1 3TA, UK
Fax: +44(1865)285002; e-Mail: david.hodgson@chem.ox.ac.uk;
b GlaxoSmithKline, Medicines Research Centre, Gunnels Wood Road, Stevenage SG1 2NY, UK
Further Information

Publication History

Received 29 March 2009
Publication Date:
12 May 2009 (online)

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Abstract

Reaction of N-(2-chloroethylidene)-tert-butylsulfin­amide with Grignard reagents or organoceriums gives terminal N-tert-butylsulfinyl aziridines in good yields and (mainly with organoceriums) good diastereomeric ratios. Oxidation of terminal N-tert-butylsulfinyl aziridines provides synthetically useful terminal N-Bus (Bus = tert-butylsulfonyl) aziridines.

Key words

aziridines - chiral auxiliaries - imines - nucleophilic addition­ - organoceriums

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