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Enantiocomplementary C–H Bond Hydroxylation Combining Photo‐Catalysis and Whole‐Cell Biocatalysis in a One‐Pot Cascade Process
Author(s) -
Peng Yongzhen,
Li Danyang,
Fan Jiajie,
Xu Weihua,
Xu Jian,
Yu Huilei,
Lin Xianfu,
Wu Qi
Publication year - 2020
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201901682
Subject(s) - chemistry , hydroxylation , biocatalysis , cascade , yield (engineering) , stereoselectivity , photoredox catalysis , catalysis , combinatorial chemistry , cascade reaction , alkyl , organic chemistry , stereoisomerism , reaction mechanism , enzyme , photocatalysis , chromatography , materials science , metallurgy
Enantiocomplementary hydroxylation of alkyl aromatics through a one‐pot photo‐biocatalytic cascade reaction is described. The photoredox process is implemented in aqueous phase with O 2 as oxidant and the subsequent ( R )‐ or ( S )‐selective bioreduction is performed by whole cell system without the addition of the expensive cofactor (NADPH). This mild, operationally simple protocol transforms a wide variety of readily available aromatic compounds into valuable chiral alcohols with high yield (up to 90 %) and stereoselectivity (up to 99 %), thereby displaying important potentials in organic synthesis.
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