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Access to Unnatural α-Amino Acids via Visible-Light-Mediated Decarboxylative Conjugate Addition to Dehydroalanine. 2020

Akshay A Shah, and Michael J Kelly, and James J Perkins
Department of Discovery Chemistry, Merck & Company, Inc., 770 Sumneytown Pike, West Point, Pennsylvania 19486, United States.

An expedient synthesis of β-alkyl α-amino acids is reported via application of decarboxylative photocatalysis. The method utilizes abundant, diverse, and inexpensive carboxylic acids to provide radicals for conjugate addition to dehydroalanine ester. High-throughput experimentation revealed an acridinium-based photocatalyst, tetraMeO-Acri-N-diMeOPh, to be the optimal choice enabling a general method that is tolerant to a wide range of functional groups. A scalable batch protocol and a parallel library synthesis for accessing diverse unnatural α-amino acids are described.

UI MeSH Term Description Entries
D003653 Decarboxylation The removal of a carboxyl group, usually in the form of carbon dioxide, from a chemical compound. Decarboxylations
D000409 Alanine A non-essential amino acid that occurs in high levels in its free state in plasma. It is produced from pyruvate by transamination. It is involved in sugar and acid metabolism, increases IMMUNITY, and provides energy for muscle tissue, BRAIN, and the CENTRAL NERVOUS SYSTEM. Abufène,Alanine, L-Isomer,L-Alanine,Alanine, L Isomer,L Alanine,L-Isomer Alanine
D000596 Amino Acids Organic compounds that generally contain an amino (-NH2) and a carboxyl (-COOH) group. Twenty alpha-amino acids are the subunits which are polymerized to form proteins. Amino Acid,Acid, Amino,Acids, Amino
D055668 Photochemical Processes Chemical reactions effected by light. Processes, Photochemical

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