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Synthesis of β-Substituted γ-Aminobutyric Acid Derivatives Through Enantioselective Photoredox Catalysis

Synthesis of β-Substituted γ-Aminobutyric Acid Derivatives Through Enantioselective Photoredox Catalysis

Jiajia Ma, Jiahui Lin, Lifang Zhao, Klaus Harms, Michael Marsch, Xiulan Xie, Eric Meggers

Angew Chem Int Ed Engl. 2018 Aug 27;57(35):11193-11197.

PMID: 29714818

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.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP56122-A	γ-Aminobutyric acid		56-12-2	Price

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