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
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
收藏
页码:16859 / 16863
页数:5
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