Catalytic asymmetric alkylation in water in the presence of surfactants: influence of the nature of the nucleophile and the allylic acetate on the activity and enantioselectivity

A symmetric palladium-catalyzed alkylation of 1,3-diphenyl-2-propenyl acetate with carbon and nitrogen nucleophiles occurs in water in the presence of a surfactant, a base, and Binap as the chiral ligand. Enantioselectivities up to 91% were obtained using carbon nucleophiles, and 93% using nitrogen nucleophiles, in the presence of CTHASO, as the surfactant. While the efficiency of the catalyst was higher in water in the presence of the surfactant in the case of carbon nucleophiles, no micellar effects were observed using the nitrogen nucleophiles. The alkylation was extended to other allylic acetates, but the efficiency as well the enantioselectivity of the coupling were lower. (C) 2003 Elsevier Ltd. All rights reserved.