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Synthesis of β-Deuterated Amino Acids via Palladium-Catalyzed H/D Exchange...

by Honghai Zhang
Publication Type
Journal
Journal Name
The Journal of Organic Chemistry
Publication Date
Page Numbers
16084 to 16089
Volume
87
Issue
23

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.