Radical‐Mediated C−H Alkylation of Glycine Derivatives: A Straightforward Strategy for Diverse α‐Unnatural Amino Acids. Issue 45 (29th September 2022)

• Record Type: Journal Article
• Authors: Hari Babu, Madala; Sim, Jaehoon
• Is Part Of: European journal of organic chemistry. Volume 2022:Issue 45(2022)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2022-09-29
• Subjects: C−H alkylation -- Glycine -- Radical addition -- Radical coupling -- Unnatural amino acids; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.202200859
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: Unnatural amino acids are important scaffolds for novel drug candidates, and especially α‐alkyl amino acids have emerged as a valuable variant. This is due to the ubiquity of alkyl groups, which are pervasive as key motifs in natural products, biological and pharmaceutical molecules. The development of radical‐based approaches in organic synthesis has expanded dramatically in recent years. It has enabled site‐ and region‐specific installation of a variety of functionalities in small molecules, which has been spontaneously applied in the preparation of versatile amino acid building blocks. The glycine motif in the backbone of amino acids has gained significant attention for allowing access to a variety of complex α‐unnatural amino acids via radical‐mediated α‐C−H alkylation. This review summarizes the last decade's development of radical‐based α‐C−H alkylation of glycine derivatives to provide unnatural α‐amino acids. The advantages, current limitations, and perspectives of glycine‐based unnatural amino acid synthesis are also discussed. Abstract : Modification of glycine is the one of the most straightforward strategy to access diverse unnatural amino acids. This review outlines an overview of recently developed transformations employing radical‐mediated C−H alkylation of N ‐aryl glycine derivatives.