Asymmetric α-Pentadienylation of Aldehydes with Cyclopropylacetylenes

Abstract

By employing readily available cyclopropylacetylene and its derivatives as the pentadienylation reagent, an asymmetric regioselective asymmetric α-pentadienylation reaction of aldehydes is developed by cooperative catalysis of a chiral Pd(0) catalyst and a chiral Brønsted acid in the presence of a subschoichmetric amount of an achiral amine. α-Pentadienylated aldehydes are afforded with high yields and enantioselectivities as well as excellent E/Z ratios.