ChemInform Abstract: Kinetic Resolution of Racemic 2-Substituted 3-Cyclopenten-1-ols by Lipase-Catalyzed Transesterifications: A Rational Strategy to Improve Enantioselectivity.
Abstract
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ChemInform Abstract
The enantioselectivity of the title reaction is not only effected by solvent (diisopropylether is the best) but also by the acylating agent. In case of alcohol (I), enantioselectivity is high with several vinyl esters, especially vinyl butyrate, but low with vinyl trifluoroacetate. In case of alcohol (II) enantioselectivity is excellent in all cases, except with vinyl pivalate. Thus, the acyl group, transiently attached at the active site of lipase catalyst, acts as stereochemical controller.
