Stereoselective metal-free catalytic synthesis of chiral trifluoromethyl aryl and alkyl amines. 2013

Andrea Genoni, and Maurizio Benaglia, and Elisabetta Massolo, and Sergio Rossi
Dipartimento di Chimica, Università di Milano, Via Golgi 19, 20133, Milano, Italy. maurizio.benaglia@unimi.it.

The enantioselective organocatalytic reduction of trifluoromethyl aryl and alkyl ketoimines afforded the corresponding fluorinated amines with high chemical and stereochemical efficiency. The Lewis base catalyzed reaction with trichlorosilane led to chiral products with a trifluoromethyl group directly linked to the newly generated stereocenter typically in >90% yield and up to 98% e.e.

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