Sequential perfluoroalkylation and asymmetric reduction of nitriles triggered with perfluoroalkyl titanates: catalytic asymmetric synthesis of perfluoroalkyl amines

Highly enantio-enriched perfluoroalkyl amines are shown to be synthesized by perfluororalkylation and asymmetric reduction of nitriles. Perfluoroalkylation of nitriles can be attained by the Lewis acidic perfluoroalkyl titanate reagents to give acyclic ketimines. Catalytic asymmetric hydrogenation of the acyclic ketimines affords the perfluoroalkyl amine products in up to 93% ee. (C) 2010 Elsevier Ltd. All rights reserved.