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Volumn 54, Issue 7, 1998, Pages 1255-1275

Transition metal-catalyzed intramolecular [4+2] cycloadditions: Mechanistic and synthetic investigations

Author keywords

[No Author keywords available]

Indexed keywords

METAL; NICKEL;

EID: 0032510192     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)10223-X     Document Type: Article
Times cited : (71)

References (62)
  • 1
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    • Toward the ideal synthesis: Connectivity analysis and multibond-forming processes
    • Hudlicky, T., Ed.; JAI Press: Greenwich, CT
    • 1. For a discussion of strategy level reactions in synthesis design, see: Wender, P. A.; Miller, B. L. Toward the Ideal Synthesis: Connectivity Analysis and Multibond-Forming Processes. In Organic Synthesis: Theory and Applications; Hudlicky, T., Ed.; JAI Press: Greenwich, CT, 1993; Vol. 2, pp 27-66.
    • (1993) Organic Synthesis: Theory and Applications , vol.2 , pp. 27-66
    • Wender, P.A.1    Miller, B.L.2
  • 2
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    • 2. For a method to circumvent this problem, see: Wender, P. A.; Correia, C. R. D. J. Am. Chem. Soc. 1987, 109, 2523-2525. For a lead reference on successful photo-induced [4 + 4] cycloadditions, see: Sieburth, S. McN.; Cunard, N. T. Tetrahedron 1996, 52, 6251-6282.
    • (1987) J. Am. Chem. Soc. , vol.109 , pp. 2523-2525
    • Wender, P.A.1    Correia, C.R.D.2
  • 3
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    • 2. For a method to circumvent this problem, see: Wender, P. A.; Correia, C. R. D. J. Am. Chem. Soc. 1987, 109, 2523-2525. For a lead reference on successful photo-induced [4 + 4] cycloadditions, see: Sieburth, S. McN.; Cunard, N. T. Tetrahedron 1996, 52, 6251-6282.
    • (1996) Tetrahedron , vol.52 , pp. 6251-6282
    • Sieburth, S.McN.1    Cunard, N.T.2
  • 4
  • 5
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    • For extensions to nitrogen-containing systems see: (b) Wender, P. A.; Smith, T. E. J. Org. Chem. 1996, 61, 824-825.
    • (1996) J. Org. Chem. , vol.61 , pp. 824-825
    • Wender, P.A.1    Smith, T.E.2
  • 6
    • 0001466031 scopus 로고
    • For the original work on intramolecular diene-diene cycloadditions, see: (c) Wender, P. A.; Ihle, N. C. J. Am. Chem. Soc. 1986, 108, 4678-4679.
    • (1986) J. Am. Chem. Soc. , vol.108 , pp. 4678-4679
    • Wender, P.A.1    Ihle, N.C.2
  • 12
  • 14
    • 0002110351 scopus 로고    scopus 로고
    • 4. Studies on metal catalyzed cycloadditions have been reported from several laboratories in recent years including those of Binger, Chiusoli, Davies, tom Dieck, Dötz, Furukawa, Grigg, Heimbach, Ito, Kreiter, Lautens, Liebeskind, Livinghouse, Matsuda, Mortreux, Motherwell, Nakamura, Negishi, Noyori, Ojima, Pirrung, Rigby, Sheridan, Smith, Stryker, Takacs, Trost, Tsuda, Tsuji, Vollhardt, Wulff, and Yamamoto. For lead references to these and related studies, see: (a) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49-92 and
    • (1996) Chem. Rev. , vol.96 , pp. 49-92
    • Lautens, M.1    Klute, W.2    Tam, W.3
  • 18
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    • Alkene and alkyne oligomerization, cooligomerization and telomerization reactions
    • Wilkinson, G.; Stone, F. G. A.; Abel, E., Eds.; Pergamon: New York, Ch. 52
    • (c) Keim, W.; Behr, A.; Röper, M. Alkene and Alkyne Oligomerization, Cooligomerization and Telomerization Reactions. in Comprehensive Organometallic Chemistry; Wilkinson, G.; Stone, F. G. A.; Abel, E., Eds.; Pergamon: New York, 1982; Vol. 8, Ch. 52, pp 371-462.
    • (1982) Comprehensive Organometallic Chemistry , vol.8 , pp. 371-462
    • Keim, W.1    Behr, A.2    Röper, M.3
  • 21
    • 84940643310 scopus 로고
    • 7. For representative reports of intermolecular [4 + 2] cycloadditions catalyzed by transition metals other than nickel, see: Iron: (a) tom Dieck, H.; Diercks, R. Angew. Chem. Int. Ed. Eng. 1983, 22, 778-779.
    • (1983) Angew. Chem. Int. Ed. Eng. , vol.22 , pp. 778-779
    • Tom Dieck, H.1    Diercks, R.2
  • 26
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    • Jpn. Pat. 6930489
    • Manganese: (f) Maruzen Oil Co., Ltd, Jpn. Pat. 6930489 (Chem. Abstr. 1970, 72, 66484).
    • (1970) Chem. Abstr. , vol.72 , pp. 66484
  • 27
    • 0000048482 scopus 로고
    • Trost, B. M., Fleming, I., Eds.; Pergamon: New York
    • 8. For a recent review of the intramolecular Diels-Alder reaction, see: Roush, W. R. in Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: New York, 1991; Vol. 5, pp. 513-550.
    • (1991) Comprehensive Organic Synthesis , vol.5 , pp. 513-550
    • Roush, W.R.1
  • 32
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    • Wilkinson, G.; Stone, F. G. A.; Abel, E. W., Eds.; Pergamon: New York, Ch. 37
    • 13. For a review of nickel-catalyzed cycloadditions of 1,3-dienes, alkenes, and alkynes, see: Jolly, P. W. in Comprehensive Organometallic Chemistry: Wilkinson, G.; Stone, F. G. A.; Abel, E. W., Eds.; Pergamon: New York, 1982, Vol 6, Ch. 37, pp 1-231.
    • (1982) Comprehensive Organometallic Chemistry , vol.6 , pp. 1-231
    • Jolly, P.W.1
  • 39
    • 0010708319 scopus 로고    scopus 로고
    • note
    • 2 were also prepared, however the olefination procedure gave only trace amounts of the desired dienyne products in these cases.
  • 41
    • 0010708320 scopus 로고    scopus 로고
    • note
    • 3) and fluoro-(X = F) substituted dienynes were also prepared from the corresponding phosphonates in 67% and 44% yields, respectively. The nickel-catalyzed cycloadditions of these substrates both proceeded in 73% yield.
  • 42
    • 0010658890 scopus 로고    scopus 로고
    • note
    • 3C- and F-substituted dienynes were completely unaffected by prolonged heating at 250 °C.
  • 43
    • 0010743104 scopus 로고    scopus 로고
    • note
    • 24. The rates of cycloaddition of the trifluoromethyl- and fluoro-substituted dienynes relative to the unsubstituted case were measured to be 0.75 and 0.63, respectively.
  • 49
    • 0010662418 scopus 로고    scopus 로고
    • note
    • 4-diene also would explain this conservation of stereochemistry. The observed reactivity differences for the methyl-substituted stubstrates, however, are less easly accommodated by such a model.
  • 52
    • 0010743790 scopus 로고    scopus 로고
    • note
    • 1H NMR with a characteristic trans coupling constant of 13.7 Hz.
  • 60
    • 0010703637 scopus 로고    scopus 로고
    • note
    • 39. Purchased from Sigma Chemical Company.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.