Abstract
A general asymmetric allylic alkylation of ester enolate equivalents at the carboxylic acid oxidation state is reported. N-Acylbenzoxazolinone-derived enol carbonates are synthesized in good yield and employed in the palladium-catalyzed alkylation reaction. Good yields (up to 99%) and enantioselectivities (up to 99% ee) are obtained and the imide products are readily converted to a series of carboxylic acid derivatives without loss of enantiopurity. High enantioselectivity in the reaction is achieved by a new strategy for ligand design involving variation of the steric properties of the diarylphosphine moiety.