Application of a one-pot lipase resolution strategy for the synthesis of chiral gamma- and delta-lactones

作者：Kamal A^*; Sandbhor M; Shaik AA

来源：Tetrahedron: Asymmetry , 2003, 14(11): 1575-1580.

DOI：10.1016/S0957-4166(03)00281-7

A successful one-pot reduction of gamma-ketoesters, delta-ketoesters and lactones to the corresponding 1,4- and 1,5-diols followed by a lipase catalyzed kinetic resolution coupled with hydrolysis to afford optically active diols is described. The synthetic utility of this one-pot method was illustrated by the oxidation of these chiral diols to respective chiral gamma-butyrolactone and delta-lactones. Lipase from Pseudomonas cepacia, immobilized on ceramic afforded the product with high enantiomeric excess in good yields under mild reaction conditions. This approach has been used to develop a convenient enantioselective route for several gamma- and delta-lactones using achiral and corresponding racemic starting material.

• 出版日期2003-6-6