Enantioselective rhodium-catalyzed allylic alkylation of acyclic α-alkoxy substituted ketones using a chiral monodentate phosphite ligand

A highly enantioselective rhodium-catalyzed allylic alkylation of acyclic α-alkoxy aryl ketones utilizing the complex derived from Wilkinson's catalyst and the chiral monodentate phosphite, BINOL-MeOP, has been developed. This process represents the first enantioselective rhodium-catalyzed allylic substitution with a prochiral nucleophile. The ability to transform the aryl ketones into the corresponding alcohol and ester illustrates the potential utility of this transformation for target directed synthesis.