Abstract
Optically active diastereomeric β-hydroperoxy esters 4 have been prepared by singlet oxygen ene reaction of β,γ-unsaturated esters 3 and subsequent horseradish peroxidase (HRP) catalyzed kinetic resolution of the ene product. The highest enantiomeric excess (up to 95%) has been obtained for the isopropyl ester threo-4c, which establishes that the size of the remote ester functionality exercises appreciable control in the enantioselectivity of the enzymatic kinetic resolution.
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