Catalytic Route to the Synthesis of Optically Active β,β-Difluoroglutamic Acid and β,β-Difluoroproline Derivatives

β,β-Difluorinated amino acid derivatives were synthesized via Mg(0)-promoted defluorination of α-trifluoromethyl iminoester. Bromination of the difluoroenamine afforded the bromodifluoromethyl iminoester in good yield. Pd-catalyzed asymmetric hydrogenation of the bromodifluoromethyl iminoester and t...

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Veröffentlicht in:Journal of organic chemistry 2004-07, Vol.69 (15), p.5132-5134
Hauptverfasser: Suzuki, Atsushi, Mae, Masayuki, Amii, Hideki, Uneyama, Kenji
Format: Artikel
Sprache:eng
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Zusammenfassung:β,β-Difluorinated amino acid derivatives were synthesized via Mg(0)-promoted defluorination of α-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 β,β-difluoroglutamic acid and β,β-difluoroproline derivatives.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo049789c