메뉴 건너뛰기




Volumn 79, Issue 2, 2014, Pages 571-581

One-pot synthesis of 3-azido- and 3-aminopiperidines by intramolecular cyclization of unsaturated amines

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL COMPOUNDS;

EID: 84896766412     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo4022666     Document Type: Article
Times cited : (43)

References (96)
  • 34
    • 0000788623 scopus 로고    scopus 로고
    • Examples Of Metal-catalyzed Transformations See
    • Examples of metal-catalyzed transformations, see: (a) Muller, T. E.; Beller, M. Chem. Rev. 1998, 98, 675.
    • (1998) Chem. Rev. , Issue.98 , pp. 675
    • Muller, T.E.1    Beller, M.2
  • 47
    • 84874233580 scopus 로고    scopus 로고
    • Kong, W.; Feige, P.; de Haro, T.; Nevado, C.
    • Kong, W.; Feige, P.; de Haro, T.; Nevado, C. Angew. Chem., Int. Ed. 2013, 52, 2469.
    • (2013) Angew. Chem., Int. Ed. , vol.52 , pp. 2469
  • 59
    • 77956047152 scopus 로고    scopus 로고
    • For a recent review on aziridium ring-opening reactions, see: examples, see
    • For a recent review on aziridium ring-opening reactions, see: (a) Metro, T. X.; Duthion, B.; Pardo, D. G.; Cossy, J. Chem. Soc. Rev. 2010, 39, 89. examples, see:
    • (2010) Chem. Soc. Rev. , vol.39 , pp. 89
    • Metro, T.X.1    Duthion, B.2    Pardo D.G Cossy, J.3
  • 83
    • 84896800705 scopus 로고    scopus 로고
    • See the Supporting Information for details. (a) NMR spectra analysis of 2a indicated the azide occupies the equatorial position in its chair conformation. The assignment is based on the characteristic coupling constant of vicinal protons in the chair conformation, such as Jaxial axial, Jequatorial axial, Jequatorial equatorial
    • See the Supporting Information for details. (a) NMR spectra analysis of 2a indicated the azide occupies the equatorial position in its chair conformation. The assignment is based on the characteristic coupling constant of vicinal protons in the chair conformation, such as Jaxial axial, Jequatorial axial, Jequatorial equatorial.
  • 84
    • 84896768275 scopus 로고    scopus 로고
    • Similarly, the NMR spectra analysis indicated the relative stereochemistry of azide is at the equatorial position for the major isomer of 6-membered endo ring-opened products 2a-2c, and 2g-2p
    • Similarly, the NMR spectra analysis indicated the relative stereochemistry of azide is at the equatorial position for the major isomer of 6-membered endo ring-opened products 2a-2c, and 2g-2p.
  • 85
    • 84896798531 scopus 로고    scopus 로고
    • Regioselectivity for 6-endo-cyclization product was observed in refs 4f and n
    • Regioselectivity for 6-endo-cyclization product was observed in refs 4f and n.
  • 92
    • 84896754931 scopus 로고    scopus 로고
    • Likely 3-isothiocyanatopiperidine is the thermodynamic product, while the formation of thiocyanatopiperidine is reversible under current conditions
    • Likely 3-isothiocyanatopiperidine is the thermodynamic product, while the formation of thiocyanatopiperidine is reversible under current conditions.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.