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Asymmetric Synthesis of 1,4‐Dicarbonyl Compounds from Aldehydes by Hydrogen Atom Transfer Photocatalysis and Chiral Lewis Acid Catalysis
Author(s) -
Kuang Yulong,
Wang Kai,
Shi Xiangcheng,
Huang Xiaoqiang,
Meggers Eric,
Wu Jie
Publication year - 2019
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201910414
Subject(s) - synthon , enantioselective synthesis , chemistry , catalysis , lewis acids and bases , photocatalysis , atom economy , hydrogen atom , lewis acid catalysis , rhodium , chiral lewis acid , combinatorial chemistry , organic chemistry , alkyl
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 ).