Facile one-pot synthesis of cinchona alkaloid-based P,N ligands and their application to Pd-catalyzed asymmetric allylic alkylation

A novel class of bidentate chiral RN donor ligands based on cinchona alkaloids is described. These ligands are easily synthesized in one-pot from commercially available enantiopure 1,2-dipheiiyl-1,2-ethanediol and cinchona alkaloids in two steps. Their application to the palladium(II)-catalyzed asymmetric allylic alkylation of 1,3-diphenyl-2-propenyl acetate gave the corresponding products in excellent yields and up to 94% ee. The effect of ligands, Substrates, nucleophiles, and temperature on the reaction was also investigated. (C) 2008 Elsevier Ltd. All rights reserved.