Chiral Bronsted acid-catalyzed regio- and enantioselective arylation of α,β-unsaturated trifluoromethyl ketones

The interesting examples of chiral phosphoric acid-catalyzed regio- and enantioselective arylation of alpha,beta-unsaturated trifluoromethyl ketones were reported. The reaction proceeded well and the desired products were obtained in good yields (up to 99%) with moderate to good enantioselectivities (up to 88% ee). Several desired products were obtained with excellent optical purities after a single recrystallization. Subsequent reduction of enantiopure products with NaBH4 afforded two diastereomers of chiral trifluoromethyl-substituted secondary alcohols with high enantioselectivities (98% ee). (C) 2010 Elsevier Ltd. All rights reserved.