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

Autor: Sheng, Fei-Fei, Gu, Jian-Guo, Liu, Kai-Hui, Zhang, Hong-Hai
Zdroj: The Journal of Organic Chemistry; December 2022, Vol. 87 Issue: 23 p16084-16089, 6p
Abstrakt: 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.
Databáze: Supplemental Index