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Volumn 68, Issue 20, 2003, Pages 7845-7852

Synthesis of octahydroquinolines through the Lewis acid catalyzed reaction of vinyl allenes and imines

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LEWIS ACID;

EID: 0141765934     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo034480z     Document Type: Article
Times cited : (38)

References (44)
  • 25
    • 0000730407 scopus 로고
    • Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, UK
    • Imines have been used as heterodienophiles in inter- and intramolecular Diels-Alder reactions. The reaction conditions depend on the nature of the substituents on the imine. Simple, neutral imines need the presence of Lewis acids to react with electron-rich dienes. For leading references, see: Weinreb, S. M. Heterodienophile Additions to Dienes in Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, UK, 1991; Vol. 5, pp 401-449.
    • (1991) Heterodienophile Additions to Dienes in Comprehensive Organic Synthesis , vol.5 , pp. 401-449
    • Weinreb, S.M.1
  • 29
    • 0141780955 scopus 로고    scopus 로고
    • note
    • The propargyl alcohols were prepared by the addition of the lithium acetylide of 1-ethynylcyclohexene to the corresponding aldehyde or ketone in tetrahydrofuran at low temperature.
  • 30
    • 0026733221 scopus 로고
    • The preparation of this vinyl allene by other methods has been reported: (a) Konoike, T.; Araki, Y. Tetrahedron Lett. 1992, 33, 5093.
    • (1992) Tetrahedron Lett. , vol.33 , pp. 5093
    • Konoike, T.1    Araki, Y.2
  • 33
    • 0007296723 scopus 로고
    • Also see ref 13b
    • The preparation of vinyl allene 8 has been reported previously: Baudouy, R.; Delbecq, F.; Gore, J. Tetrahedron 1980, 36, 189. Also see ref 13b.
    • (1980) Tetrahedron , vol.36 , pp. 189
    • Baudouy, R.1    Delbecq, F.2    Gore, J.3
  • 38
    • 0141669046 scopus 로고    scopus 로고
    • note
    • 13C) and bidimensional (COSY, HSQC, HMBC) NMR experiments.
  • 40
    • 0141780954 scopus 로고    scopus 로고
    • note
    • We thank one of the reviewers for helpful discussions in regard to this problem.
  • 41
    • 0141557664 scopus 로고    scopus 로고
    • note
    • 13C NMR spectrum. See the Supporting Information for copies of the NMR spectra.
  • 42
    • 0141446115 scopus 로고    scopus 로고
    • note
    • The geometry of the double bonds in the ene compounds was assigned on the basis of the ROESY spectra of compounds 33-36.
  • 43
    • 0003802667 scopus 로고
    • University of Utrecht, The Netherlands
    • Spek, A. L. PLATON92, University of Utrecht, The Netherlands, 1992.
    • (1992) Platon92
    • Spek, A.L.1
  • 44
    • 0141557665 scopus 로고    scopus 로고
    • See the Supporting Information for the X-ray data
    • See the Supporting Information for the X-ray data.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.