Mild and efficient boronic acid catalysis of Diels-Alder cycloadditions to 2-alkynoic acids

被引：49

作者：

Zheng, Hongchao ^{[1
]}

Hall, Dennis G. ^{[1
]}

机构：

[1] Univ Alberta, Dept Chem, Gunning Lemieux Chem Ctr, Edmonton, AB T6G 2G2, Canada

来源：

TETRAHEDRON LETTERS | 2010年 / 51卷 / 27期

基金：

加拿大自然科学与工程研究理事会;

关键词：

CARBOXYLIC-ACIDS; PHENYLBORONIC ACID; GOLD; ORGANOCATALYSIS; ACTIVATION;

D O I：

10.1016/j.tetlet.2010.04.132

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The concept of boronic acid catalysis (BAC) for the activation of unsaturated carboxylic acids is applied to the Diels-Alder cycloaddition between 2-alkynoic acids as dienophiles and various dienes. These [4+2] cycloadditions produce cyclohexadienyl carboxylic acids, which can be oxidized in situ to produce polysubstituted aromatic carboxylic acids. The boronic acid catalyst is suspected to provide activation by a LUMO-lowering effect of the unsaturated carboxylic acid likely via a covalent, monoacylated hemiboronic ester intermediate. (C) 2010 Elsevier Ltd. All rights reserved.

引用

页码：3561 / 3564

页数：4

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