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

New homochiral l-norbornanesulfenic and sulfonic acid derivatives 2-7, as w ell as the sulfonic acids 8, are easily synthesised starting from 2-methyle ne-l -norbornylthiotriflates 1. This new class of homochiral bridgehead thi osulfonates 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. (C) 2000 Elsevier Science Ltd. All right s reserved.