The Friedel-Crafts reactions of chiral N-(2,2,2-trifluoroethylidene)-1-aryl
ethylamines 1a and 1b with various electron-rich aromatic compounds were ex
amined. The reactions proceeded readily at room temperature in the presence
of BF3.Et2O. Substituted products 2-12 were obtained in low to very high s
tereo selectivities (up to 100% d.e.). The absolute configuration of compou
nd 12 was determined by X-ray analysis. Moreover, the chiral auxiliary from
compounds 3 and 12 was selectively removed by palladium-catalyzed hydrogen
olysis. (C) 2001 Elsevier Science Ltd. All rights reserved.