Synthesis of β‐Substituted γ‐Aminobutyric Acid Derivatives through Enantioselective Photoredox Catalysis |
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Authors: | Jiajia Ma Jiahui Lin Lifang Zhao Dr. Klaus Harms Michael Marsch Dr. Xiulan Xie Prof. Dr. Eric Meggers |
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Affiliation: | Fachbereich Chemie, Philipps-Universit?t Marburg, Marburg, Germany |
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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. |
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Keywords: | γ -aminobutyric acid asymmetric catalysis quaternary stereocenters radical addition visible-light catalysis |
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