Sulfinyl group as an intramolecular nucleophile: synthesis of bromohydrins from beta-methyl-gamma,delta-unsaturated sulfoxides with high 1,2-asymmetric induction.

Abstract

Bromohydrins have been prepared from beta-methyl-gamma,delta-unsaturated sulfoxides with high regio- and stereoselectivity. The reaction proceeds via neighboring group participation of the sulfinyl moiety with inversion of sulfoxide configuration as proven by an (18)O labeling study and X-ray crystallography.