Chemical conversion of cyclic alpha-amino acids to cyclic alpha-aminophosphonic acids.
The oxidative decarboxylation of cyclic alpha-amino acids having urethane-type N-protecting groups with lead tetraacetate [Pb(OAc)4] gave 2-hydroxy derivatives, which were transformed into the corresponding alpha-aminophosphonic acid esters by treatment of trialkyl phosphites in the presence of Lewis acids. Deprotection and ester cleavage of the products in the usual manner afforded cyclic alpha-aminophosphonic acids. The convenient chemical conversion of five- and six-membered cyclic alpha-amino acids to the corresponding cyclic alpha-aminophosphonic acids has been accomplished.
Kaname
M
M
Faculty of Pharmaceutical Sciences of Hokuriku University, Kanazawa, Japan.
Mashige
H
H
Yoshifuji
S
S
D000598:Amino Acids, Cyclic / Q000737:chemistry*; D003653:Decarboxylation; D006868:Hydrolysis; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D063065:Organophosphonates / Q000737:chemistry*
D000598:Amino Acids, Cyclic; D007202:Indicators and Reagents; D063065:Organophosphonates