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Volumn 128, Issue 40, 2006, Pages 13130-13141

Interplay of structure and reactivity in a most unusual furan Diels-Alder reaction

Author keywords

[No Author keywords available]

Indexed keywords

CURTIN HAMMETT MECHANISM; ENERGY BARRIERS; LEWIS ACID BINDING;

EID: 33749532305     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja061458p     Document Type: Article
Times cited : (43)

References (119)
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    • De Souza, M.V.N.1
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    • For reviews describing other important synthetic strategies, see: (f) Rozen, S. Eur. J. Org. Chem. 2005, 2433.
    • (2005) Eur. J. Org. Chem. , pp. 2433
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  • 35
    • 0029889487 scopus 로고    scopus 로고
    • (b) Non-fluorinated dienophiles related structurally to 9b have been reported, but they react only with the more reactive dienes; see: Funk, R. L.; Yost, K. J. J. Org. Chem. 1996, 61, 2598.
    • (1996) J. Org. Chem. , vol.61 , pp. 2598
    • Funk, R.L.1    Yost, K.J.2
  • 50
  • 52
    • 0038060240 scopus 로고    scopus 로고
    • Catalytic asymmetric Diels-Alder reactions
    • Kobayashi, S., Jørgensen, K. A., Eds.; Wiley VCH: Weinheim; Chapter 1
    • Hayashi, Y. Catalytic Asymmetric Diels-Alder Reactions. In Cycloaddition Reactions in Organic Synthesis; Kobayashi, S., Jørgensen, K. A., Eds.; Wiley VCH: Weinheim, 2002; Chapter 1, pp 5-53.
    • (2002) Cycloaddition Reactions in Organic Synthesis , pp. 5-53
    • Hayashi, Y.1
  • 56
    • 0001869942 scopus 로고
    • Schaefer, H. F., Ed.; Plenum Press: New York
    • (a) Dunning, T. H.; Hay, P. J. In Modern Theoretical Chemistry; Schaefer, H. F., Ed.; Plenum Press: New York, 1977, Vol. 3, pp 1-27.
    • (1977) Modern Theoretical Chemistry , vol.3 , pp. 1-27
    • Dunning, T.H.1    Hay, P.J.2
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    • note
    • The preliminary screen was described in ref 10a; further results are described in the Supporting Information.
  • 93
    • 0037039943 scopus 로고    scopus 로고
    • Domingo, L. R.; Aurell, M. J. J. Org. Chem. 2002, 67, 959. The regiochemistry of the cycloaddition between a masked ortho-benzoquinone and 2-methylfuran was studied previously by DFT. Our results are consistent with the reported outcomes.
    • (2002) J. Org. Chem. , vol.67 , pp. 959
    • Domingo, L.R.1    Aurell, M.J.2
  • 96
    • 33749530342 scopus 로고    scopus 로고
    • Unpublished results, personal communication to J.M.P.
    • Westermaier, M.; Mayr, H. Unpublished results, personal communication to J.M.P.
    • Westermaier, M.1    Mayr, H.2
  • 97
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    • note
    • 13 looked for evidence of reversibility in the Diels-Alder reaction and found none, so we believe that the treatment of the reactions as essentially irreversible under kinetic control is justified.
  • 105
    • 4143091851 scopus 로고    scopus 로고
    • (f) For the computational construction of an alkene electrophilicity scale, see: Domingo, L. R.; Perez, P.; Contreras, R. Tetrahedron 2004, 60, 6585.
    • (2004) Tetrahedron , vol.60 , pp. 6585
    • Domingo, L.R.1    Perez, P.2    Contreras, R.3
  • 106
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    • For recent applications of this powerful tool, see: (a) Lee, K.; Sung, D. D. Curr. Org. Chem. 2004, 8, 557.
    • (2004) Curr. Org. Chem. , vol.8 , pp. 557
    • Lee, K.1    Sung, D.D.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.