Palladium-catalyzed allylic nucleophilic substitution reactions of (E)-gamma-acetoxy-alpha,beta-unsaturated p-tolylsulfoxides

Regio- and diastereoselective nucleophilic allylic substitutions of optical ly pure (E)-gamma -acetoxy-x,beta -unsaturated p-tolyl-sulfoxides 2 and 3 w ith sodium dimethyl malonate have been carried out. The reactivity of these substrates is controlled by both the chiral sulfinyl group and the size of the alkyl group attached at the gamma -terminus of the allylic system. Thi s process constitutes an example of palladium-mediated resolution of 1:1 mi xture of acetates 2 and 3. (C) 2001 Elsevier Science Ltd. All rights reserv ed.