Stereo- and regiocontrolled synthesis of fluorohydrins from optically active epoxides

Article abstract of DOI:10.1016/S0957-4166(00)82254-5

The hydrofluorination of optically active terminal epoxides, which were produced by a microbial reaction, with HF-amine reagents weer 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.