Carboxylic Acids as A Traceless Activation Group for Conjugate Additions: A Three-Step Synthesis of (±)-Pregabalin

被引：492

作者：

Chu, Lingling ^{[1
]}

Ohta, Chisa ^{[1
]}

Zuo, Zhiwei ^{[1
]}

MacMillan, David W. C. ^{[1
]}

机构：

[1] Princeton Univ, Merck Ctr Catalysis, Princeton, NJ 08544 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2014年 / 136卷 / 31期

关键词：

DNA CROSS-LINKING; RADICAL REACTIONS; INVENTION; DECARBOXYLATION; HOMOLOGATION; CHEMISTRY; AUXILIARY; ESTERS; SALTS;

D O I：

10.1021/ja505964r

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The direct application of carboxylic acids as a traceless activation group for radical Michael additions has been accomplished via visible light-mediated photo-redox catalysis. Photon-induced oxidation of a broad series of carboxylic acids, including hydrocarbon-substituted, alpha-oxy, and alpha-amino acids, provides a versatile CO2-extrusion platform to generate Michael donors without the requirement for organometallic activation or propagation. A diverse array of Michael acceptors is amenable to this new conjugate addition strategy. An application of this technology to a three-step synthesis of the medicinal agent pregabalin (commercialized by Pfizer under the trade name Lyrica) is also presented.

引用

页码：10886 / 10889

页数：4

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