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

Sterically hindered and enantiomerically pure beta-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 beta-amino alcohols catalyze an efficient enantio selective sulfoxidation of alkyl aryl sulfides, while enantioselectivities as high as 96% ee can be observed in the sulfoxidation of benzyl aryl sulfides. (c) 2005 Elsevier Ltd. All rights reserved.