Regio- and Stereoselective Preparation of β,γ-Unsaturated Carboxylic Acids by One-Pot Sequential Double 1,6-Addition of Grignard Reagents to Methyl Coumalate

被引：15

作者：

Plevova, Kristina ^{[1
]}

Chang, Liang ^{[1
]}

Martin, Emmeline ^{[1
]}

Llopis, Quentin ^{[1
]}

Dechoux, Luc ^{[1
]}

Thorimbert, Serge ^{[1
]}

机构：

[1] UPMC Univ Paris 06, Sorbonne Univ, Inst Parisien Chim Mol, CNRS,UMR 8232, 4 Pl Jussieu, F-75005 Paris, France

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2016年 / 358卷 / 20期

关键词：

double 1,6-conjugate addition; 6-pi electrocyclic ring opening; Grignard reagents; metal catalysis; unsaturated acids; ASYMMETRIC CONJUGATE ADDITION; CROSS-COUPLING REACTIONS; DIELS-ALDER REACTIONS; CARBON-DIOXIDE; 1,6-CONJUGATE ADDITION; ORGANOCOPPER REAGENTS; ORGANIC-SYNTHESIS; 2-PYRONES; 2H-PYRAN-2-ONES; NUCLEOPHILES;

D O I：

10.1002/adsc.201600212

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

An efficient regio- and stereoselective metal-catalyzed addition of two Grignard reagents (homo-coupling, 2 RMgX or hetero-coupling, (RMgX)-Mg-1+(RMgX)-Mg-2) to methyl coumalate (methyl 2-oxo-2H-pyran-5-carboxylate) is described. This synthetic approach opens the access to a wide variety of functionalized beta,gamma-unsaturated carboxylic acids in a modular way. Control of the chemo- and stereoselectivity of this one-pot procedure is discussed.

引用

页码：3293 / 3297

页数：5