Ring opening of disubstituted epoxides linked to a secondary oxygen group with an organocopper reagent

被引：3

作者：

Terayama, Naoki ^{[1
]}

Ushijima, Shodai ^{[1
]}

Yasui, Eiko ^{[1
]}

Miyashita, Masaaki ^{[1
]}

Nagumo, Shinji ^{[1
]}

机构：

[1] Kogakuin Univ, Dept Appl Chem, Hachioji, Tokyo 1920015, Japan

来源：

TETRAHEDRON LETTERS | 2014年 / 55卷 / 48期

关键词：

Epoxy ring opening; Epoxide linked to secondary alcohol; Regioselectivity; Trimethylsilyl; Gilman reagent; PHOSPHORIC-ACID; MECHANISM; ESTERS; ROUTE;

D O I：

10.1016/j.tetlet.2014.09.029

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Coupling reactions of epoxide linked to a secondary oxygen group with Gilman reagents were examined. The regiochemical direction depended on whether there is TMS or MOM as a protective group of the secondary alcohol. anti-Epoxy alcohol 6 tended to react with Me2CuLi at the C4 position to generate 1,2-diol 22 as a major component. Epoxide 7 linked to a trimethylsilyloxy group displayed selective formation of 1,3-dioL 18. On the other hand, the reactions of syn-epoxy alcohol 12 and the corresponding TMS ether 13 resulted in the selective formation of 1,2-diol 25. (C) 2014 Elsevier Ltd. All rights reserved.

引用

页码：6515 / 6519

页数：5

共 24 条

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