Facile synthesis of homochiral derivatives of 10-bornane sulfinates, sulfinamides and sulfinimines

摘要

A convenient route for the synthesis of enantiopure 10-bornanesulfinic acid derivatives from (1S)-camphorsulfonyl chloride is described. An interesting epimerization at sulfur in five-membered sultines is observed, leading to diastereoisomerically pure (S_S)-10-isobornyl sulfinates. A large difference in solubility in organic solvents allowed (R_S)-2-ox-10-bornanesulfinamide to be obtained as the major diastereoisomer. Cyclization of 2-oxo-10-bornanesulfinamides gave five-membered sulfinimines.