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

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 eosin Y hydr...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2019-11, Vol.58 (47), p.16859-16863
Main Authors: Kuang, Yulong, Wang, Kai, Shi, Xiangcheng, Huang, Xiaoqiang, Meggers, Eric, Wu, Jie
Format: Article
Language:English
Subjects:
Aldehydes
Asymmetric synthesis
Atom economy
Carbonyl compounds
Catalysis
Catalysts
Enantiomers
eosin Y
hydrogen atom transfer
Lewis acid
Natural products
Photocatalysis
radical umpolung
Rhodium
Synthesis
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Summary: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 eosin Y 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). It takes two: Enantioselective synthesis of 1,4‐dicarbonyl compounds directly from readily available aldehydes was accomplished with good yield and enantioselectivity through the synergistic combination of a neutral eosin Y hydrogen atom transfer photocatalyst and a bis‐cyclometalated rhodium catalyst.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201910414