Enzymatic kinetic resolution studies of racemic 4-hydroxycyclopent-2-en-1-one using Lipozyme IM (R)

Enzymatic kinetic resolution studies of (+/-)-4-hydroxycyclopent-2-en-1-one 2 were taken up in organic solvents by transesterification with vinyl acet ate and alcoholysis of its acetate 3 as an alternative to the desymmetrizat ion of meso-cyclopentenediol to provide faster and economic access to enant iomerically pure 4-(R)tert-butyldimethylsilyloxycyclopent-2-en-1-one 1. Par ameters were screened using Lipozyme IM(R) as catalyst. Although enantiosel ectivity observed was moderate (E=24, by alcoholysis of 3 with 2-butanol), trends in the effect of solvent, water content and alcohol structure showed useful directions for screening of other enzymes for optimization of the m ethod to useful levels of efficiency. (C) 1999 Elsevier Science Ltd. All ri ghts reserved.