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Synfacts 2007(1): 0101-0101  
DOI: 10.1055/s-2006-955670
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart · New York

Aziridination of Chalcones Using Tertiary Amine Catalysts

Contributor(s): Benjamin List, Subhas Chandra Pan
Y.-M. Shen, M.-X. Zhao, J. Xu, Y. Shi*
Colorado State University, Fort Collins, USA
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Publication History

Publication Date:
15 December 2006 (online)

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Significance

The authors report an aziridination of chalcones using in situ generated aminimides. They have found that N-methylmorpholine (1) along with o-mesitylenesulfonylhydroxyl­amine (MSH) in the presence of base generates an effective aminimide reagent for the aziridination of different aromatic and heteroaromatic chalcones (42-85% yield). The authors have also shown an asymmetric aziridination using Tröger’s base (2) as the chiral tertiary amine (50-90% yield, er = 78:22 to 83:17).