Asymmetric synthesis of epibatidine by use of a novel enantioselective sulfinate elimination reaction

Abstract

A vicinal bis-sulfone having the 7-azabicyclo[2.2.1]heptane skeleton undergoes a novel type of asymmetric elimination on treatment with the sodium alkoxide derivative of ( 1R, 2S)-ephedrine, to give an alkenyl sulfone product, which is a key intermediate in the synthesis of the alkaloid epibatidine.