Stereo- and regiocontrolled synthesis of fluorohydrins from optically active epoxides
作者:Junko Umezawa、Osamu Takahashi、Keizo Furuhashi、Hiroyuki Nohira
DOI:10.1016/s0957-4166(00)82254-5
日期:1993.1
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
研究了由微生物反应产生的旋光性末端环氧化物与HF-胺试剂的氢氟化作用。1,2-环氧辛烷和缩水甘油基己醚制得相应的2-氟-1-链烷醇衍生物,具有不对称中心的高立体定向性,而在五氟苯乙烯氧化物和2-甲基-1,2-环氧己烷的氢氟化反应中,部分消旋化发生。所用胺的碱性,HF-胺试剂中的HF /胺比以及环氧化物上的取代基影响环氧化物氢氟化的立体定向性和区域选择性。