Enantiospecific synthesis of substituted 1-norbornanesulfonic acids and 1-norbornanesulfenic and sulfonic acid derivatives

Abstract

New homochiral 1-norbornanesulfenic and sulfonic acid derivatives 2–7, as well as the sulfonic acids 8, are easily synthesised starting from 2-methylene-1-norbornylthiotriflates 1. This new class of homochiral bridgehead thiosulfonates was prepared by us from naturally occurring (+)-camphor and (−)-fenchone. Nucleophilic substitution at the sulfenyl sulfur atom is the key step for this synthetic strategy