Synthesis of optically active partly gem-difluorinated allylic alcohols via [2,3]-Wittig rearrangements and lipase-catalyzed reaction

被引：20

作者：

Itoh, T

Kudo, K

Tanaka, N

Sakabe, K

Takagi, Y

Kihara, H

机构：

[1] Okayama Univ, Fac Educ, Dept Chem, Okayama 7008530, Japan

[2] Hyogo Univ Teachers Educ, Dept Nat Sci, Yashiro, Hyogo 6731494, Japan

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 23期

关键词：

2,3]-Wittig rearrangement; partly gem-difluorinated allylic alcohols; lipase-catalyzed reaction; asymmmetric synthesis;

D O I：

10.1016/S0040-4039(00)00640-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[2,3]-Wittig rearrangement of 1,1,2-trifluoroallylic ethers gave five types of novel 4,4,5-trifluoroalk-1,5-dien-3-ols. The rearrangement reaction gave the alcohols with perfect (E)*-selection over the newly created olefin bond for two substrates. Lipase-catalyzed optical resolution of 4,4,5-trifluoroalk-1,5-dien-3-ols was successfully performed to afford optically active partly gem-difluorinated allylic alcohols for the first time. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：4591 / 4595

页数：5

共 12 条

[1] The generation of difluoroenolates from trifluoroethanol and reproducible syntheses of α,α-difluoro-β-hydroxy ketones [J].