Synthesis of optically active aminooxy alcohols

Racemic secondary alcohols with an N-protected oxyamino function in the bet a -position were prepared by a base-catalyzed epoxide ring opening with N-h ydroxyphthalimide or acetone oxime. The enantiomers were separated with a g ood selectivity by a lipase-catalyzed acetylation of the racemates with vin yl acetate. The protecting group of the aminooxy alcohol was split off by a hydrochloric acid hydrolysis to yield the hydrochloride of one of the enan tiomeric forms of the title compounds. (C) 2001 Elsevier Science B.V. All r ights reserved.