Photoredox Catalytic Installation of an Alkyl/Aryl Side Chain and Deuterium into (<i>S</i>)-Methyleneoxazolidinone: Synthesis of Enantioenriched α-Deuterated α-Amino Acid Derivatives
Yue Dong, Meng Xiang, Giri Gnawali, Mengyang Chang, Wei Wang
Abstract
A photoredox catalytic asymmetric method has been established for the installation of both aliphatic and aromatic side chains and the introduction of deuterium into the chiral methyleneoxazolidinone simultaneously. Efficient coupling of readily available boronic acids with the chiral auxiliary delivers structurally diverse α-deuterated α-amino acid derivatives with a high level of diastereoselectivity and deuteration.
Topics & Concepts
ChemistrySide chainDeuteriumAlkylArylCatalysisCombinatorial chemistryAmino acidEnantioselective synthesisOrganic chemistryBoronic acidBiochemistryPolymerPhysicsQuantum mechanicsChemical Reactions and IsotopesAmmonia Synthesis and Nitrogen ReductionAsymmetric Hydrogenation and Catalysis