Asymmetric Synthesis of 1,4-Dicarbonyl Compounds from Aldehydes via the Marriage of Hydrogen Atom Transfer Photocatalysis with Chiral Lewis Acid Catalysis.

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2019
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Abstract
Enantioenriched 1,4-dicarbonyl compounds are versatile synthons in natural product and pharmaceutical drug synthesis. We herein report a mild pathway for an efficient enantioselective synthesis of these compounds directly from aldehydes through the synergistic cooperation of a neutral eosin Y hydrogen atom transfer photocatalyst and a chiral rhodium Lewis acid catalyst. This protocol is distinguished by its operational simplicity, abundant feedstocks, atom-economy, and generating products in high yields (up to 99%) and high enantioselectivities (up to 99%  ee ).
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Authors Kuang, Yulong;Wang, Kai;Shi, Xiangcheng;Huang, Xiaoqiang;Meggers, Eric;Wu, Jie;
Journal angewandte chemie (international ed in english)
Year 2019
DOI
10.1002/anie.201910414
URL
Keywords
asymmetric synthesis bis-cyclometalated rhodium(iii) complex hydrogen atom transfer neutral eosin y radical umpolung

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