Iron-Catalyzed Regio- and Stereoselective Substitution of γ,δ-Epoxy-α,β-unsaturated Esters and Amides with Grignard Reagents

被引：19

作者：

Hata, Takeshi ^{[1
]}

Bannai, Rie ^{[1
]}

Otsuki, Mamoru ^{[1
]}

Urabe, Hirokazu ^{[1
]}

机构：

[1] Tokyo Inst Technol, Grad Sch Biosci & Biotechnol, Dept Biomol Engn, Midori Ku, Kanagawa 2268501, Japan

来源：

ORGANIC LETTERS | 2010年 / 12卷 / 05期

关键词：

ALPHA; BETA-UNSATURATED GAMMA; DELTA-EPOXY ESTERS; NUCLEOPHILIC-SUBSTITUTION; DOUBLE INVERSION; METHYLATION; ALKYLATION; PHOSPHATES; REDUCTION; EPOXIDES; ALCOHOLS;

D O I：

10.1021/ol100022w

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

When gamma,delta-epoxy-alpha,beta-unsaturated esters or amides were treated with 2 equiv of Grignard reagents in the presence of 10-24 mol % FeCl2, regio- and stereoselective substitution of the epoxide moiety with the Grignard reagent occurred to give exclusively delta-hydroxy-gamma-alkyl or aryl-alpha,beta-unsaturated esters or amides in good yields.

引用

页码：1012 / 1014

页数：3

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