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Highly efficient asymmetric reduction of 2-benzylidenecyclopentanone derivatives to give selectively the exocyclic allylic alcohols in ee's up to 96% was performed with chiral oxazaborolidine-based catalysts. Complete enantioselectivity furnishing (S)-configured alcohol product can be achieved by bioreduction of 2-(4-chlorobenzylidene)cyclopentanone with Daucus carota root. The synthesized compounds can serve as enantiomerically enriched standards for the monitoring of the enzyme-catalyzed redox processes.