Catalytic route to the synthesis of optically active beta,beta-difluoroglutamic acid and beta,beta-difluoroproline derivatives.
Beta,beta-difluorinated amino acid derivatives were synthesized via Mg(0)-promoted defluorination of alpha-trifluoromethyl iminoester. Bromination of the difluoroenamine afforded the bromodifluoromethyl iminoester in good yield. Pd-catalyzed asymmetric hydrogenation of the bromodifluoromethyl iminoester and the subsequent transformations provided optically active beta,beta-difluoroglutamic acid and beta,beta-difluoroproline derivatives.
Suzuki
Atsushi
A
Department of Applied Chemistry, Faculty of Engineering, Okayama University, 3-1-1 Tsushimanaka, Okayama 700-8530, Japan.
Mae
Masayuki
M
Amii
Hideki
H
Uneyama
Kenji
K
D002384:Catalysis; D005971:Glutamates / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D011392:Proline / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry
D005971:Glutamates; C065405:3,3-difluoroglutamate; D011392:Proline