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Synthesis of β‐Substituted γ‐Aminobutyric Acid Derivatives through Enantioselective Photoredox Catalysis
Author(s) -
Ma Jiajia,
Lin Jiahui,
Zhao Lifang,
Harms Klaus,
Marsch Michael,
Xie Xiulan,
Meggers Eric
Publication year - 2018
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201804040
Subject(s) - enantioselective synthesis , stereocenter , chemistry , combinatorial chemistry , catalysis , conjugate , organic chemistry , mathematical analysis , mathematics
β‐Substituted chiral γ‐aminobutyric acids feature important biological activities and are valuable intermediates for the synthesis of pharmaceuticals. Herein, an efficient catalytic enantioselective approach for the synthesis of β‐substituted γ‐aminobutyric acid derivatives through visible‐light‐induced photocatalyst‐free asymmetric radical conjugate additions is reported. Various β‐substituted γ‐aminobutyric acid analogues, including previously inaccessible derivatives containing fluorinated quaternary stereocenters, were obtained in good yields (42–89 %) and with excellent enantioselectivity (90–97 % ee ). Synthetically valuable applications were demonstrated by providing straightforward synthetic access to the pharmaceuticals or related bioactive compounds ( S )‐pregabalin, ( R )‐baclofen, ( R )‐rolipram, and ( S )‐nebracetam.