Synthesis of sterically controlled chiral β-amino alcohols and their application to the catalytic asymmetric sulfoxidation of sulfides

Abstract

Sterically hindered and enantiomerically pure β-amino alcohols 8a and 8b were prepared from the enantiomerically pure aziridine-2-carboxylic acid menthol ester 13. Vanadium complexes of the chiral Schiff-base ligands prepared from the β-amino alcohols catalyze an efficient enantioselective sulfoxidation of alkyl aryl sulfides, while enantioselectivities as high as 96% ee can be observed in the sulfoxidation of benzyl aryl sulfides.