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Synfacts 2007(1): 0058-0058  
DOI: 10.1055/s-2006-955721
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Stereoselective Synthesis of N-Alkylaziridines from N-Chloroamines

Contributor(s): Hisashi Yamamoto, Matthew B. Boxer
S. P. Bew*, D. L. Hughes, N. J. Palmer, V. Savic, K. M. Soapi, M. A. Wilson
University of East Anglia, Norwich and Biofocus Discovery Ltd., Saffron Walden, UK
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Publication History

Publication Date:
15 December 2006 (online)

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Significance

The authors report the first synthesis of cis- and trans-N-alkylaziridines from N-chloro­amines. Along with this, the group showed a relatively straightforward synthesis of the chromatographically stable N-chloroamines, which has not always been thought of as a simple task. Deprotonation of the N-chloroamine substrates gave the cyclized aziridines in moderate to high yield with good diastereoselectivities.