ASYMMETRIC REDUCTION OF KETOXIME ETHERS TO OPTICALLY ACTIVE O-SUBSTITUTED HYDROXYLAMINES WITH REAGENTS PREPARED FROM BORANE AND CHIRAL AMINO ALCOHOLS

Abstract The asymmetric reduction of ketoxime ethers to yield enantiomerically enriched chiral hydroxylamines with reagents prepared from borane and norephedrine has been investigated. Very high enantioselectivity (ca. 99% ee) was obtained in the reduction of ketoxime O-( o -nitrobenzyl) ether to O-( o -nitrobenzyl) hydroxylamine.