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Volumn 47, Issue 48, 2008, Pages 9236-9239

Organocatalytic asymmetric Diels-Alder reactions of 3-vinylindoles

Author keywords

Asymmetric synthesis; Cycloaddition; Diels Alder reaction; Hydrogen bonds; Organocatalysis

Indexed keywords

CATALYSIS; ENANTIOSELECTIVITY; HYDROGEN; HYDROGEN BONDS; REACTION KINETICS; THIOUREAS; UREA;

EID: 56449130065     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200804275     Document Type: Article
Times cited : (208)

References (52)
  • 3
    • 0003544583 scopus 로고    scopus 로고
    • 2nd ed, Ed, I. Ojima, Wiley-VCH, New York
    • c) K. Maruoka in Catalytic Asymmetric Synthesis, 2nd ed. (Ed.: I. Ojima), Wiley-VCH, New York, 2000, p. 467;
    • (2000) Catalytic Asymmetric Synthesis , pp. 467
    • Maruoka, K.1
  • 4
    • 0000097153 scopus 로고    scopus 로고
    • Eds: E. N. Jacobsen, A. Pfaltz, H. Yamamoto, Springer, New York
    • d) D. A. Evans, J. S. Johnson in Comprehensive Asymmetric Catalysis, Vol. 3 (Eds: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, New York, 1999, p. 1177;
    • (1999) Comprehensive Asymmetric Catalysis , vol.3 , pp. 1177
    • Evans, D.A.1    Johnson, J.S.2
  • 17
    • 0001649881 scopus 로고    scopus 로고
    • For reviews, see: e
    • For reviews, see: e) U. Pindur, Heterocycles 1998, 27, 1253;
    • (1998) Heterocycles , vol.27 , pp. 1253
    • Pindur, U.1
  • 18
    • 0003979828 scopus 로고    scopus 로고
    • Academic Press, London
    • f) R. J. Sundberg, in Indoles, Academic Press, London, 1996, p. 156.
    • (1996) Indoles , pp. 156
    • Sundberg, R.J.1
  • 19
    • 26244443140 scopus 로고    scopus 로고
    • Recent examples: g M. Bleile, H.-H. Otto, Monatsh. Chem. 2005, 136, 1799;
    • Recent examples: g) M. Bleile, H.-H. Otto, Monatsh. Chem. 2005, 136, 1799;
  • 22
    • 0027480777 scopus 로고    scopus 로고
    • For a chiral auxiliary approach, giving the cycloadducts in modest (less than 50%) yields, see: U. Pindur, G. Lutz, G. Fischer, D. Schollmeyer, W. Massa, L. Schröder, Tetrahedron 1993, 49, 2863.
    • For a chiral auxiliary approach, giving the cycloadducts in modest (less than 50%) yields, see: U. Pindur, G. Lutz, G. Fischer, D. Schollmeyer, W. Massa, L. Schröder, Tetrahedron 1993, 49, 2863.
  • 23
    • 0346865819 scopus 로고    scopus 로고
    • Reviews on catalysis through hydrogen-bonding interactions: a
    • Reviews on catalysis through hydrogen-bonding interactions: a) P. R. Schreiner, Chem. Soc. Rev. 2003, 32, 289;
    • (2003) Chem. Soc. Rev , vol.32 , pp. 289
    • Schreiner, P.R.1
  • 37
    • 47049125893 scopus 로고    scopus 로고
    • and references therein
    • Angew. Chem. Int. Ed. 2008, 47, 4016, and references therein.
    • (2008) Angew. Chem. Int. Ed , vol.47 , pp. 4016
  • 40
    • 0024849710 scopus 로고
    • For Diels, Alder reactions of anthrones, see: c
    • For Diels - Alder reactions of anthrones, see: c) O. Riant, H. B. Kagan, Tetrahedron Lett. 1989, 30, 7403;
    • (1989) Tetrahedron Lett , vol.30 , pp. 7403
    • Riant, O.1    Kagan, H.B.2
  • 42
    • 56449096365 scopus 로고    scopus 로고
    • See the Supporting Information
    • See the Supporting Information.
  • 45
    • 56449111032 scopus 로고    scopus 로고
    • The double bond is stabilized at the 3,4-position by conjugation with the aromatic ring. After trifluoroacetylation the doublebond shift, which requires double-bond protonation, is highly disfavored. See ref. [3i].
    • The double bond is stabilized at the 3,4-position by conjugation with the aromatic ring. After trifluoroacetylation the doublebond shift, which requires double-bond protonation, is highly disfavored. See ref. [3i].
  • 46
    • 56449131330 scopus 로고    scopus 로고
    • This acid-sensitive diene underwent extensive decomposition
    • This acid-sensitive diene underwent extensive decomposition.
  • 47
    • 0026591285 scopus 로고    scopus 로고
    • The E-isomer can more easily access the s-cis conformation, which is necessary for the reaction to occur following a Diels-Alder pathway, thus giving evidence for a concerted [4+2] mechanism for this cycloaddition. See:U. Pindur, M.-H. Kim, M. Rogge, W. Massa, M. Molinier, J. Org. Chem. 1992, 57, 910.
    • The E-isomer can more easily access the s-cis conformation, which is necessary for the reaction to occur following a Diels-Alder pathway, thus giving evidence for a concerted [4+2] mechanism for this cycloaddition. See:U. Pindur, M.-H. Kim, M. Rogge, W. Massa, M. Molinier, J. Org. Chem. 1992, 57, 910.
  • 50


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.