Enantioselective preparation of (R) and (S)-3-hydroxycyclopentanone by kinetic resolution

A straightforward approach to enantiomerically enriched (R) and (S)-3-hydroxycyclopentanone is described. The key step involves a kinetic resolution of racemic 3-hydroxycyclopentanone using commercial Pseudomonas cepacia lipase immobilized on diatomite (Amano lipase PS-DI). The absolute stereochemistry of the product was determined by derivatization into (R)-3-(benzyloxy)cyclopentanone.

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► Efficient preparation of optically pure 3-hydroxycyclopentanone.
► Kinetic resolution by lipase catalyzed acylation with vinyl acetate.
► Kazlauskas’ rule ambiguous with small cyclic substrates.
► Absolute stereochemistry confirmed by derivatization.