Thiocrown ether additive effects on diastereoselectivity of the lipase- catalyzed reaction: Preparation of optically active 3-hydroxy-2- methylalkanenitriles through a double enzymatic reaction strategy

Article abstract of DOI:10.1246/bcsj.72.1589

The additive effect on diastereoselectivity towards the lipase-catalyzed hydrolysis of acetates of 3-hydroxy-2-methyl-or 3-hydroxy-2- ethylalkanenitriles has been investigated. Diastereoselectivity was not influenced by thiocrown ether additives, although a significant modification of enantioselectivity was observed. Origin of the diastereoselectivity of the lipase-catalyzed reaction was thus evidently different from that of enantioselectivity. Based on these results, an easy preparation of optically active 3-hydroxy-2-methylpentanenitrile and 3-hydroxy-2-methylbutanenitrile have been demonstrated through lipase-catalyzed reaction by a double enzymatic reaction strategy.