Synthesis of β-Deuterated Amino Acids via Palladium-Catalyzed H/D Exchange
Fei-Fei Sheng, Jianguo Gu, Kaihui Liu, Honghai Zhang
Abstract
Despite several synthetic approaches that have been developed for α-deuterated amino acids, the synthesis of β-deuterated amino acids has remained a challenge. Herein, we disclose a palladium catalyzed H/D exchange protocol for a β-deuterated N-protected amino amide, which can be converted to a β-deuterated amino acid simply by removal of protecting groups. This protocol is highly efficient, simply manipulated, and appliable for deuterium-labeling of many amino amides. In addition, deuterium labeling of phenylalanine derivatives was also successful when pivalic acid served as an additive to promote the H/D exchange process.
Topics & Concepts
DeuteriumAmino acidChemistryPalladiumPhenylalanineAmideCatalysisPivalic acidHydrogen–deuterium exchangeCombinatorial chemistryOrganic chemistryHydrogenBiochemistryQuantum mechanicsPhysicsChemical Reactions and IsotopesChemical Synthesis and AnalysisAsymmetric Hydrogenation and Catalysis