A NEW CHIRAL CATALYST FOR THE ENANTIOSELECTIVE SYNTHESIS OF SECONDARY ALCOHOLS AND DEUTERATED PRIMARY ALCOHOLS BY CARBONYL REDUCTION

Article abstract of DOI:10.1016/S0040-4039(01)93871-7

An efficient synthesis of (S)-(-)-2-(di-β-naphthylhydroxymethyl)pyrrolidine (1) makes available the oxazaborolidine derivates 2 and 3 which are excellent catalysts for borane reduction of a variety of achiral ketones to chiral secondary alcohols, e.g. acetophenone, 98percent ee; α-tetralone, 95percent ee; and methyl-4-oxo-4-phenyl butyrate, 96percent ee.The synthesis of chiral 1-deuterio primary alcohols from achiral aldehydes with B-n-butyloxazaborolidine (4) as catalyst in the presence of 2H-catecholborane as reductant has also been demonstrated, e.g. benzaldehyde, 95percent ee; cyclohexanecarboxaldehyde, 92percent ee; and n-octanal, 90percent ee.