Catalytic Asymmetric Oxidative γ-Coupling of α, β-Unsaturated Aldehydes with Air as the Terminal Oxidant

被引：31

作者：

Naesborg, Line ^{[1
]}

Corti, Vasco ^{[1
]}

Leth, Lars Astrup ^{[1
]}

Poulsen, Pernille H. ^{[1
]}

Jorgensen, Karl Anker ^{[1
]}

机构：

[1] Aarhus Univ, Dept Chem, DK-8000 Aarhus, Denmark

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2018年 / 57卷 / 06期

关键词：

asymmetric catalysis; organocatalysis; oxidative coupling; single-electron transfer; synthetic methods; ALPHA; BETA-UNSATURATED ALDEHYDES; DIENAMINE CATALYSIS; ALKYLATION; ACTIVATION; ORGANOCATALYSIS; RADICALS; OLEFINS; ETHERS; ENALS;

D O I：

10.1002/anie.201711944

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A novel concept for catalytic asymmetric coupling reactions is presented. Merging organocatalysis with single-electron oxidation by using a catalytic amount of a copper(II) salt and air as the terminal oxidant, we have developed a highly stereoselective carbon-carbon oxidative coupling reaction of alpha, beta-unsaturated aldehydes. The concept relies on the generation of a dienamine intermediate, which is oxidized to an open-shell activated species that undergoes highly selective gamma-homo- and gamma-heterocoupling reactions. In the majority of examples presented, only a single stereoisomer was formed.

引用

页码：1606 / 1610

页数：5

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