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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).
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页码:16859 / 16863
页数:5
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