Efficient lipase-catalyzed kinetic resolution and dynamic kinetic resolution of beta-hydroxy nitriles. A route to useful precursors for gamma-amino alcohols

An efficient kinetic resolution of racemic beta -hydroxy nitrites I was per formed via Candida antarctica lipase (N-435)-catalyzed transesterification. A variety of racemic alkyl, aryl, and aryloxymethyl substituted beta -hydr oxy nitrites was efficiently transformed to the corresponding enantiomerica lly pure acetates (ee > 99% and conversion = 50%) with E values from 40 to > 1000. The combination of the enzymatic kinetic resolution willi a rutheni um-catalyzed alcohol racemization led to a dynamic kinetic resolution (ee'S Up to 99%, Yields Up to 85%).