Photoredox Catalytic Installation of an Alkyl/Aryl Side Chain and Deuterium into (S)-Methyleneoxazolidinone: Synthesis of Enantioenriched α-Deuterated α-Amino Acid Derivatives

A photoredox catalytic asymmetric method has been establishedforthe installation of both aliphatic and aromatic side chains and theintroduction of deuterium into the chiral methyleneoxazolidinone simultaneously.Efficient coupling of readily available boronic acids with the chiralauxiliary delivers structurally diverse alpha-deuterated alpha-aminoacid derivatives with a high level of diastereoselectivity and deuteration.

Automated summary

A photoredox catalytic asymmetric method is developed to introduce both aliphatic and aromatic side chains and deuterium into chiral methyleneoxazolidinone simultaneously. The coupling of readily available boronic acids with the chiral auxiliary yields structurally diverse alpha-deuterated alpha-amino acid derivatives with high diastereoselectivity and deuteration.