The borane-chiral oxazoborolidine complexes were prepared from (S)-(-)-2-(1-pyrrolidino)-1,1-diphenylpropan-1-ol (1a) and (S)-(-)-2- (1-pyrrolidino)-1,1,3-triphenylpropan-1-ol (1b) with borane in THF, respectively. These reagents were used in asymmetric reduction of C=N double bonds of aliphatic and aromatic ketoxime ethers to yield chiral primary amines, which are (S)-configuration in most of the cases, with chemical yields (52~76%) and optical yields (6~99%). The effects of the structures of substrates and enantioselectivity were also discussed.

Key words: STEREOSELECTIVITY, BORANE, PROPANOL P, ASYMMETRY, REDUCTION REACTION, PYRROLE P, BENZENE P