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Synfacts 2006(2): 0131-0131  
DOI: 10.1055/s-2005-924777
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Cu-Catalyzed Enantioselective Aziridination of Chalcones

Contributor(s): Mark Lautens, Y. Eric Fang
L. Ma, D.-M. Du, J. Xu*
Peking University, P. R. of China
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Publication History

Publication Date:
23 January 2006 (online)

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Significance

CuOTf-catalyzed asymmetric aziridination of chalcones using PhI=NTs affords moderate to good yield of the product in good to excellent enantioselectivities. The chiral ligand is a modified version of the BOX ligand, in which the bite angle has been modified by attaching bisoxazoline on 1,2-cyclohexane. Out of three possible diastereomers of the two stereogenic centers (asterisk), the (S,S)-cyclohexane and (S)-phenyloxazoline are the matched combination, giving optimal results superior to the BOX ligand. Noth electron-withdrawing or electron-donating groups are tolerated.