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Volumn 129, Issue 9, 2008, Pages 767-774

Synthesis of Ψ[CH(RF)NH]Gly-peptides: The dramatic effect of a single fluorine atom on the diastereocontrol of the key aza-Michael reaction

Author keywords

Aza Michael; Electronegativity; Fluorine; Fluoroalkyl; Peptide bond surrogate; Peptidomimetics

Indexed keywords


EID: 50549087165     PISSN: 00221139     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jfluchem.2008.06.018     Document Type: Article
Times cited : (15)

References (22)
  • 8
    • 42949127288 scopus 로고    scopus 로고
    • For a review on the trifluoroethylamine unit, see:
    • For a review on the trifluoroethylamine unit, see:. Sani M., Volonterio A., and Zanda M. ChemMedChem 2 (2007) 1693-1700
    • (2007) ChemMedChem , vol.2 , pp. 1693-1700
    • Sani, M.1    Volonterio, A.2    Zanda, M.3
  • 14
    • 42949153522 scopus 로고    scopus 로고
    • For a preliminary report of this work see:
    • For a preliminary report of this work see:. Bigotti S., Volonterio A., and Zanda M. Synlett (2008) 958-962
    • (2008) Synlett , pp. 958-962
    • Bigotti, S.1    Volonterio, A.2    Zanda, M.3
  • 17
    • 34848848499 scopus 로고    scopus 로고
    • For a recent analysis of this issue see:
    • For a recent analysis of this issue see:. Müller K., Faeh C., and Diederich F. Science 317 (2007) 1881-1886
    • (2007) Science , vol.317 , pp. 1881-1886
    • Müller, K.1    Faeh, C.2    Diederich, F.3
  • 18
    • 50549104646 scopus 로고    scopus 로고
    • Nitro-alkene 2 was prepared starting from a commercially available aqueous solution of fluoral hydrate, whereas nitro-alkenes 3-7 were synthetized from fluoro-acetaldehyde hemiacetals prepared by reduction of the corresponding esters:
    • Nitro-alkene 2 was prepared starting from a commercially available aqueous solution of fluoral hydrate, whereas nitro-alkenes 3-7 were synthetized from fluoro-acetaldehyde hemiacetals prepared by reduction of the corresponding esters:
  • 20
    • 50549102519 scopus 로고    scopus 로고
    • CCDC 687809.
    • CCDC 687809.
  • 21
    • 50549099601 scopus 로고    scopus 로고
    • 19F NMR signals of the fluorinated group of the major diasteroisomers 9 were always observed at higher fields than those of the minor diastereoisomer 10 (see Experimental Section).
    • 19F NMR signals of the fluorinated group of the major diasteroisomers 9 were always observed at higher fields than those of the minor diastereoisomer 10 (see Experimental Section).
  • 22
    • 35349019315 scopus 로고    scopus 로고
    • For a recent mechanistic investigation on a related Michael reaction involving fluorinated acrylamide acceptors:
    • For a recent mechanistic investigation on a related Michael reaction involving fluorinated acrylamide acceptors:. Fustero S., Chiva G., Piera J., Volonterio A., Zanda M., Gonzalez J., and Ramallal A.M. Chem. Eur. J. 13 (2007) 8530-8542
    • (2007) Chem. Eur. J. , vol.13 , pp. 8530-8542
    • Fustero, S.1    Chiva, G.2    Piera, J.3    Volonterio, A.4    Zanda, M.5    Gonzalez, J.6    Ramallal, A.M.7


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.