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Volumn 7, Issue 10, 2005, Pages 2003-2005

Phosphine-mediated coupling of gramines with aldehydes: A remarkably simple synthesis of 3-vinylindoles

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE DERIVATIVE; GRAMINE; INDOLE DERIVATIVE; TRIBUTYLPHOSPHINE; VINYL DERIVATIVE;

EID: 19544370894     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol050484+     Document Type: Article
Times cited : (36)

References (37)
  • 1
    • 0001649881 scopus 로고
    • For a review on chemistry of vinylindoles, see: Pindur, U. Heterocycles 1988, 27, 1253-1268.
    • (1988) Heterocycles , vol.27 , pp. 1253-1268
    • Pindur, U.1
  • 10
    • 0003979828 scopus 로고    scopus 로고
    • Academic Press: San Diego, Chapter 11
    • For an overview of synthetically useful methods for the preparation of 3-vinylindoles, see: Sundberg, R. J. Indoles; Academic Press: San Diego, 1996; Chapter 11.
    • (1996) Indoles
    • Sundberg, R.J.1
  • 15
    • 0027450633 scopus 로고
    • Suzuki couplings of indole-3-boronic acids with vinyl triflates have also been employed: Zheng, Q.; Yang, Y.; Martin, A. R. Tetrahedron Lett. 1993, 34, 2235-2238.
    • (1993) Tetrahedron Lett. , vol.34 , pp. 2235-2238
    • Zheng, Q.1    Yang, Y.2    Martin, A.R.3
  • 26
    • 3543120622 scopus 로고
    • a value for deprotonation of the benzylic position of benzyltriphenylphosphonium cation is 17.4: Zhang, X.-M.; Bordwell, F. G. J. Am. Chem. Soc. 1994, 116, 968-972.
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 968-972
    • Zhang, X.-M.1    Bordwell, F.G.2
  • 27
    • 0000778826 scopus 로고
    • a units less acidic than their triphenylphosphonium counterparts: Johnson, A. W.; LaCount, R. B. Tetrahedron 1960, 9, 130-138.
    • (1960) Tetrahedron , vol.9 , pp. 130-138
    • Johnson, A.W.1    LaCount, R.B.2
  • 28
    • 19544389035 scopus 로고    scopus 로고
    • note
    • 3 in acetonitrile at 80°C gave rise to 7.
  • 29
    • 0001848341 scopus 로고
    • For a review on stereochemical and mechanistic aspects of the Wittig reaction, see: Maryanoff, B. E.; Reitz, A. B. Chem. Rev. 1989, 89, 863-927.
    • (1989) Chem. Rev. , vol.89 , pp. 863-927
    • Maryanoff, B.E.1    Reitz, A.B.2
  • 33
    • 19544368359 scopus 로고    scopus 로고
    • note
    • We thank Dr. P. Ruggiero for performing these experiments.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.