Chiral Brønsted acid-catalyzed diastereo- and enantioselective synthesis of CF3-substituted aziridines

Zhuo Chai; Jean-Philippe Bouillon; Dominique Cahard

doi:10.1039/C2CC35246J

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Chemical Communications

Issue 76, 2012

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Chiral Brønsted acid-catalyzed diastereo- and enantioselective synthesis of CF₃-substituted aziridines

Zhuo Chai,^a Jean-Philippe Bouillon^a and Dominique Cahard*^a

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UMR CNRS 6014 C.O.B.R.A., Université et INSA de Rouen, 1 rue Tesnière, 76821 Mont Saint Aignan, France
E-mail: dominique.cahard@univ-rouen.fr ;
Tel: 33 235522466

Chem. Commun., 2012,48, 9471-9473

DOI: 10.1039/C2CC35246J
Received 20 Jul 2012, Accepted 03 Aug 2012
First published online 06 Aug 2012

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A multicomponent organocatalyzed highly diastereo- and enantioselective synthesis of CF₃-substituted aziridines is described. This reaction of in situ generated CF₃CHN₂ and aldimines was realized by chiral Brønsted acid catalysis. The utility of the products is illustrated by easy access to β-CF₃ isocysteine and aziridine-containing dipeptides.

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Chiral Brønsted acid-catalyzed diastereo- and enantioselective synthesis of CF₃-substituted aziridines