Sulfur-containing β-amino alcohols as catalysts in enantioselective synthesis

Article abstract of DOI:10.1016/S0957-4166(97)00193-6

Oxazaborolidine catalysts generated in situ from cyclic or acyclic sulfur containing (R)-cysteine, (S)-penicillamine and (S)-methionine derivates and BH₃ have been applied successfully to the enantiocontrolled, catalytic reduction of aromatic ketones. The corresponding sec alcohols could be obtained in excellent enantiomeric excess, up to 100% ee. Using these chiral auxiliaries in the enantioselective addition of diethylzinc to aldehydes afforded optically active sec alcohols in enantiomeric excess up to 93% ee.