Tetrahedron: Asymmetry

Stereo-and regiocontrolled synthesis of fluorohydrins from optically active epoxides

J Umezawa, O Takahashi, K Furuhashi…

Index: Umezawa; Takahashi; Furuhashi; Nohira Tetrahedron Asymmetry, 1993 , vol. 4, # 9 p. 2053 - 2060

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Citation Number: 33

Abstract

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. ...

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