TY - JOUR
T1 - Facile synthesis of DL-4,4-difluoroornithine, DL-4,4-difluoroglutamine, and γ-DL-4,4-difluoroglutamyl-containing peptides
T2 - Regiospecific addition of nucleophiles to N-Cbz-di-tert-butyl-DL-4,4-difluoroglutamate
AU - Tsukamoto, Takashi
AU - Coward, James K.
PY - 1996/4/5
Y1 - 1996/4/5
N2 - The reaction of several nucleophiles with N-Cbz-protected di-tert-butyl-DL-4,4-difluoroglutamate was investigated as an approach to the synthesis of various fluorinated amino acids and peptides. The γ-carboxyl group is highly activated by the two adjacent fluorine atoms, and nucleophilic reactions occurred exclusively at that carbonyl carbon. Further transformations of the reaction products resulted in the synthesis of DL-4,4-difluoroornithine, DL-4,4-difluoroglutamine, and γ-DL-4,4-difluoroglutamyl-contoining dipeptides.
AB - The reaction of several nucleophiles with N-Cbz-protected di-tert-butyl-DL-4,4-difluoroglutamate was investigated as an approach to the synthesis of various fluorinated amino acids and peptides. The γ-carboxyl group is highly activated by the two adjacent fluorine atoms, and nucleophilic reactions occurred exclusively at that carbonyl carbon. Further transformations of the reaction products resulted in the synthesis of DL-4,4-difluoroornithine, DL-4,4-difluoroglutamine, and γ-DL-4,4-difluoroglutamyl-contoining dipeptides.
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U2 - 10.1021/jo952044+
DO - 10.1021/jo952044+
M3 - Article
AN - SCOPUS:0029969542
SN - 0022-3263
VL - 61
SP - 2497
EP - 2500
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 7
ER -