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
K. Mitsukura et al., 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, B CHEM S J, 72(7), 1999, pp. 1589-1595
The additive effect on diastereoselectivity towards the lipase-catalyzed hy
drolysis of acetates of 3-hydroxy-2-methyl- or 3-hydroxy-2-ethylalkanenitri
les has been investigated. Diastereoselectivity was not influenced by thioc
rown ether additives, although a significant modification of enantioselecti
vity was observed. Origin of the diastereoselectivity of the lipase-catalyz
ed reaction was thus evidently different from that of enantioselectivity. B
ased on these results, an easy preparation of optically active 3-hydroxy-2-
methylpentanenitrile and 3-hydroxy-2-methylbutanenitrile have been demonstr
ated through lipase-catalyzed reaction by a double enzymatic reaction strat
egy.