Efficient Preparation of (R)-3-HydroxypentanenitriIe with High Enantiomeric Excess by Enzymatic Reduction with Subsequent Enhancement of the Optical Purity by Lipase-Catalyzed Ester Hydrolysis

摘要

An efficient chemo-enzymatic procedure for the synthesis of (β)-3-hydroxypentanenitrile (1) with over 99% enantiomeric excess using two enzymatic reactions was successfully established. Initial enantioselective enzymatic reduction of 3-oxopentanenitriIe with reductase SI gave (R)-with an 81.5% ee which was then converted to (β)-l-(cyanomethyl) propyl w-butyrate (3b). Subsequent lipase-catalyzed enantioselective hydrolysis of 3b gave (R)-in a high yield with over 99% ee.