Asymmetric Synthesis of 1,4-Dicarbonyl Compounds from Aldehydes by Hydrogen Atom Transfer Photocatalysis and Chiral Lewis Acid Catalysis

被引：107

作者：

Kuang, Yulong ^{[1
]}

Wang, Kai ^{[1
]}

Shi, Xiangcheng ^{[1
]}

Huang, Xiaoqiang ^{[3
]}

Meggers, Eric ^{[3
]}

Wu, Jie ^{[1
,2
]}

机构：

[1] Natl Univ Singapore, Dept Chem, 3 Sci Dr 3, Singapore 117543, Singapore

[2] Natl Univ Singapore Suzhou Res Inst, 377 Lin Quan St,Suzhou Ind Pk, Suzhou 215123, Jiangsu, Peoples R China

[3] Philipps Univ Marburg, Fachbereich Chem, Hans Meerwein Str 4, D-35043 Marburg, Germany

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2019年 / 58卷 / 47期

基金：

中国国家自然科学基金;

关键词：

asymmetric synthesis; hydrogen atom transfer; eosinY; radical umpolung; rhodium; INTERMOLECULAR STETTER REACTION; DUAL-CATALYSIS; CONVERGENT; RADICALS; NICKEL; ENALS;

D O I：

10.1002/anie.201910414

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Enantioenriched 1,4-dicarbonyl compounds are versatile synthons in natural product and pharmaceutical drug synthesis. We herein report a mild pathway for the efficient enantioselective synthesis of these compounds directly from aldehydes through synergistic cooperation between a neutral eosinY hydrogen atom transfer photocatalyst and a chiral rhodium Lewis acid catalyst. This method is distinguished by its operational simplicity, abundant feedstocks, atom economy, and ability to generate products in high yields (up to 99%) and high enantioselectivity (up to 99% ee).

引用

页码：16859 / 16863

页数：5

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