Boron Tribromide-Assisted Chiral Phosphoric Acid Catalysts for Enantioselective [2+2] Cycloaddition

Abstract

BBr₃ -assisted chiral phosphoric acid catalysts for enantioselective [2+2] cycloaddition were developed. The reactions of phenyl vinyl sulfide with α-substituted acroleins proceeded, and the corresponding [2+2] cycloadducts were obtained with high enantioselectivity. In particular, the [2+2] cycloadduct obtained from methacrolein is a synthetically useful optically active cyclobutane, which could be transformed to a key intermediate for (+)-frontalin, a pheromone of Asian elephants.

Keywords: [2+2] cycloaddition; boron Lewis acid; chiral Brønsted acid catalyst; cyclobutane; phosphoric acid.