Synthesis of optically active aminooxy alcohols

Racemic secondary alcohols with an N-protected oxyamino function in the β-position were prepared by a base-catalyzed epoxide ring opening with N-hydroxyphthalimide or acetone oxime. The enantiomers were separated with a good selectivity by a lipase-catalyzed acetylation of the racemates with vinyl acetate. The protecting group of the aminooxy alcohol was split off by a hydrochloric acid hydrolysis to yield the hydrochloride of one of the enantiomeric forms of the title compounds.