Regio- and stereoselective fluorinative ring-opening reaction of epoxyalcohols by (i-PrO)2TiF2-Et4NF-nHF.: Synthesis of optically active 3-fluoro-1,2-diols

被引：13

作者：

Hara, S ^{[1
]}

Hoshio, T ^{[1
]}

Kameoka, M ^{[1
]}

Sawaguchi, M ^{[1
]}

Fukuhara, T ^{[1
]}

Yoneda, N ^{[1
]}

机构：

[1] Hokkaido Univ, Grad Sch Engn, Div Mol Chem, Sapporo, Hokkaido 0608628, Japan

来源：

TETRAHEDRON | 1999年 / 55卷 / 16期

关键词：

asymmetric synthesis; epoxides; halogenation; halohydrins;

D O I：

10.1016/S0040-4020(99)00180-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 [有机化学]; 081704 [应用化学];

摘要：

Stereo- and regioselective ring opening reaction of epoxyalcohols was achieved by (i-PrO)(2)TiF2 and Et4NF-nHF under mild conditions. Fluoride attacked the epoxide at the C3 carbon with the inversion of the stereochemistry to give 3-fluoro-1,2-diols selectively. When optically active epoxyalcohols were used as the starting material, the corresponding 3-fluoro-1,2-diols were obtained with high optical purity. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：4947 / 4954

页数：8

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