LIPASE-CATALYZED KINETIC RESOLUTION OF BAYLIS-HILLMAN PRODUCTS

Lipase-catalyzed kinetic resolution of the various Baylis-Hillman prod ucts, alpha-methylene-beta-hydroxy compounds, were examined. When lipa se PS was used as a biocatalyst in acetonitrile, transesterification o f racemic ethyl 3-hydroxy-2-methylenebutanoate or 3-hydroxy-2-methylen epentanoate proceeded in a practical enantiomeric excess. The resoluti on by hydrolysis of the acetate derivatives was also tried. In contras t, in case of racemic ethyl 3-acetoxy-2-methylenepentanoate, under the conditions using lipase AK, the E value of the resolution was >321. ( C) 1998 Elsevier Science Ltd. All rights reserved.