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

A convenient route for the synthesis of enantiopure 10-bornanesulfinic acid derivatives from (1S)-camphorsulfonyl chloride is described. An interestin g epimerization at sulfur in five-membered sultines is observed, leading to diastereoisomerically pure (S-s)-10-isobornyl sulfinates. A large differen ce in solubility in organic solvents allowed (R-s)-2-oxo-10-bornanesulfinam ide to be obtained as the major diastereoisomer. Cyclization of 2-oxo-10-bo rnanesulfinamides gave five-membered sulfinimines. (C) 1999 Elsevier Scienc e Ltd. All rights reserved.