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Volumn 50, Issue 51, 2009, Pages 7175-7179

Diastereoselective synthesis of pyrrolidines via 1,3-dipolar cycloaddition of a chiral azomethine ylide

Author keywords

[No Author keywords available]

Indexed keywords

AZOMETHINE YLIDE; GLUCOSE; PYRROLIDINE DERIVATIVE;

EID: 70449102945     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.10.030     Document Type: Article
Times cited : (36)

References (63)
  • 1
    • 0004101860 scopus 로고
    • Padwa A. (Ed), Wiley, New York
    • In: Padwa A. (Ed). 1,3-Dipolar Cycloaddition Chemistry Vols. 1 and 2 (1984), Wiley, New York
    • (1984) 1,3-Dipolar Cycloaddition Chemistry , vol.1-2
  • 43
    • 79956190154 scopus 로고    scopus 로고
    • McGuire J.L. (Ed), Wiley-VCH, Weinheim
    • In: McGuire J.L. (Ed). Pharmaceuticals Vols. 1-4 (2000), Wiley-VCH, Weinheim
    • (2000) Pharmaceuticals , vol.1-4
  • 46
    • 0003023759 scopus 로고    scopus 로고
    • Fraser Reid B., Tatsuta K., and Thiem J. (Eds), Springer, Heidelberg
    • In: Fraser Reid B., Tatsuta K., and Thiem J. (Eds). Glycoscience: Chemistry and Chemical Biology (2001), Springer, Heidelberg
    • (2001) Glycoscience: Chemistry and Chemical Biology
  • 49
    • 0346768307 scopus 로고    scopus 로고
    • Wong C.-H. (Ed), Wiley-VCH, Weinheim
    • In: Wong C.-H. (Ed). Carbohydrate Based Drug Discovery (2003), Wiley-VCH, Weinheim
    • (2003) Carbohydrate Based Drug Discovery
  • 53
    • 70449083988 scopus 로고    scopus 로고
    • note
    • The required secondary amines 2a-b were prepared by the reaction of benzylamine with ethyl or benzyl bromoacetate in the presence of diisopropylethylamine in dichloromethane under reflux.
  • 54
    • 0032480391 scopus 로고    scopus 로고
    • For endo-selective 1,3-dipolar cycloaddition see:
    • For endo-selective 1,3-dipolar cycloaddition see:. Enders D., Meyer I., Runsink J., and Raabe G. Tetrahedron 54 (1998) 10733
    • (1998) Tetrahedron , vol.54 , pp. 10733
    • Enders, D.1    Meyer, I.2    Runsink, J.3    Raabe, G.4
  • 58
    • 5644259533 scopus 로고    scopus 로고
    • For metalcatalyzed exo-selective 1,3-dipolar cycloaddition see:
    • For metalcatalyzed exo-selective 1,3-dipolar cycloaddition see:. Peddibhotla S., and Tepe J.J. J. Am. Chem. Soc. 126 (2004) 12776
    • (2004) J. Am. Chem. Soc. , vol.126 , pp. 12776
    • Peddibhotla, S.1    Tepe, J.J.2
  • 61
    • 70449121388 scopus 로고    scopus 로고
    • 7 (580.22): C, 70.33; H, 5.56; N, 4.82. Found: C, 70.22; H, 5.52; N, 4.87.
    • 3): δ 1.43 (s, 6H), 3.41 (d, 1H, J = 13.0 Hz, -NCHH), 3.45 (dd, 1H, J = 8.5, 1.6 Hz, H-3a), 3.84 (d, 1H, J = 13.0 Hz, -NCHH), 3.86 (t, 1H, J = 8.4 Hz, H-6a), 4.25 (d, 1H, J = 2.3 Hz, H-3), 4.37 (d, 1H, J = 9.2 Hz, H-1), 5.09-5.16 (m, 3H), 5.31 (dd, 1H, J = 5.4, 2.3 Hz, H-2′), 6.07 (d, 1H, J = 5.4 Hz, H-1′), 7.22-7.26(m, 7H, Ar-H), 7.32-7.37
  • 62
    • 70449118574 scopus 로고    scopus 로고
    • note
    • Crystallographic data for the structure 5c in this Letter have been deposited with the Cambridge Crystallographic Data centre as supplemental Publication No. CCDC-689250. Copies of the data can be obtained, free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax: +44 01223 336033 or email: deposit@ccdc.cam.ac.uk).
  • 63
    • 70449114062 scopus 로고    scopus 로고
    • note
    • Crystallographic data for the structure 8c in this Letter have been deposited with the Cambridge Crystallographic Data centre as supplemental Publication No. CCDC-699267. Copies of the data can be obtained, free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax: +44 01223 336033 or email: deposit@ccdc.cam.ac.uk).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.