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Visible Light‐Induced Salan‐Copper(II)‐Catalyzed Enantioselective Aerobic α‐Hydroxylation of β‐Keto Esters
Author(s) -
Yang Fan,
Zhao Jingnan,
Tang Xiaofei,
Wu Yufeng,
Yu Zongyi,
Meng Qingwei
Publication year - 2019
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201801263
Subject(s) - chemistry , enantioselective synthesis , hydroxylation , singlet oxygen , catalysis , copper , yield (engineering) , combinatorial chemistry , organic chemistry , medicinal chemistry , oxygen , materials science , metallurgy , enzyme
A strategy of visible light‐induced salan‐copper(II)‐catalyzed asymmetric α‐hydroxylation of β‐keto ester with utilization of sustainable air as the oxidant was developed. This protocol allows convenient access to a number of enantioenriched α‐hydroxyl β‐keto esters (up to 95% yield, 96% ee), especially for β‐keto methyl esters that are valuable architectures in pharmaceuticals, including the key intermediate of the sodium‐channel blocker ( S )‐indoxacarb. Experimental studies suggest that reactive singlet oxygen may participate in this reaction.
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