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  • Title: Enantioselective synthesis of indole-based unnatural β-Alkynyl α-amino acid derivatives via chiral phosphoric acid catalysis.
    Author: Woldegiorgis AG, Gu H, Lin X.
    Journal: Chirality; 2022 Apr; 34(4):678-693. PubMed ID: 35128727.
    Abstract:
    The synthesis of unnatural α-amino acid derivatives has attracted considerable interest in recent years, as they are ubiquitous in protein synthesis and peptide-based drug discovery. Herein, we reported the chiral phosphoric acid catalyzed asymmetric reaction of indoles with β,γ-alkynyl-α-imino esters for the enantioselective synthesis of unnatural indole-based α-amino acid derivatives. This asymmetric organocatalysis protocol enables efficient synthesis of unnatural α-amino acid derivatives with a tetrasubstituted stereogenic center and an alkyne moiety with up to 99% yield and 98% ee, resulting in operationally simple conditions, short reaction time, and broad substrate scope.
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