Stereo‐ and Regiocontrolled Synthesis of Fluorohydrins from Optically Active Epoxides.

Abstract The hydrofluorination of optically active terminal epoxides, which were produced by a microbial reaction, with HF-amine reagents were studied. 1,2-Epoxyoctane and glycidyl hexyl ether gave the corresponding 2-fluoro-1-alkanol derivatives with inversion of the asymmetric center with high stereospecificity, while in the hydrofluorination of pentafluorostyrene oxide and 2-methyl-1,2-epoxyhexane, partial racemization occurred. The basicity of the amine used, the HF/amine ratio in the HF-amine reagent, and the substituent on the epoxide affected the stereospecificity and regioselectivity of the hydrofluorination of the epoxides.