A Novel and Selective Fluoride Opening of Aziridines by XtalFluor-E. Synthesis of Fluorinated Diamino Acid Derivatives
Por:
M. NONN, L. KISS, M. HAUKKA, S. FUSTERO and F. FULOP
Publicada:
6 mar 2015
Resumen:
The selective introduction of fluorine onto the skeleton of an aminocyclopentane or cyclohexane carboxylate has been developed through a novel and efficient fluoride opening of an activated aziridine ring with XtalFluor-E. The reaction proceeded through a stereoselective aziridination of the olefinic bond of a bicyclic lactam and regioselective aziridine ring opening with difluorosulfiliminium tetrafluoroborate with the neighboring group assistance of the sulfonamide moiety to yield fluorinated diamino acid derivatives. The method based on the selective aziridine opening by fluoride has been generalized to afford access to mono- or bicyclic fluorinated substances.
Filiaciones:
M. NONN:
Univ Szeged, Hungarian Acad Sci, Inst Pharmaceut Chem, H-6720 Szeged, Hungary
Univ Szeged, Hungarian Acad Sci, Stereochem Res Grp, H-6720 Szeged, Hungary
L. KISS:
Univ Szeged, Hungarian Acad Sci, Inst Pharmaceut Chem, H-6720 Szeged, Hungary
M. HAUKKA:
Univ Jyvaskyla, Dept Chem, FIN-40014 Jyvaskyla, Finland
:
Univ Valencia, Fac Farm, Dept Quim Organ, Valencia 46100, Spain
F. FULOP:
Univ Szeged, Hungarian Acad Sci, Inst Pharmaceut Chem, H-6720 Szeged, Hungary
Univ Szeged, Hungarian Acad Sci, Stereochem Res Grp, H-6720 Szeged, Hungary
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