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- Title
Synthesis of β‐Substituted γ‐Aminobutyric Acid Derivatives through Enantioselective Photoredox Catalysis.
- Authors
Ma, Jiajia; Lin, Jiahui; Zhao, Lifang; Harms, Klaus; Marsch, Michael; Xie, Xiulan; Meggers, Eric
- Abstract
Abstract: 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.
- Subjects
AMINOBUTYRIC acid; ENANTIOSELECTIVE catalysis; OXIDATION-reduction reaction; INTERMEDIATES (Chemistry); CATALYTIC activity; CHEMICAL yield
- Publication
Angewandte Chemie, 2018, Vol 130, Issue 35, p11363
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201804040