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Volumn 118, Issue 40, 1996, Pages 9597-9605

Transition metal catalyzed stereospecific intramolecular [3 + 2] cycloadditions of methylenecyclopropanes with alkynes

Author keywords

[No Author keywords available]

Indexed keywords

TETRAHYDROFURAN DERIVATIVE;

EID: 0029860853     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9611809     Document Type: Article
Times cited : (76)

References (111)
  • 1
    • 0002110351 scopus 로고    scopus 로고
    • For a review of transition metal mediated cycloadditions, see: Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49.
    • (1996) Chem. Rev. , vol.96 , pp. 49
    • Lautens, M.1    Klute, W.2    Tam, W.3
  • 2
    • 0000384028 scopus 로고
    • Trost, B. M., Ed.; Pergamon Press: Oxford
    • For a review of [3 + 2] cycloadditions, see: Chan, D. M. T. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; vol. 5, p 271;
    • (1991) Comprehensive Organic Synthesis , vol.5 , pp. 271
    • Chan, D.M.T.1
  • 3
    • 0005433149 scopus 로고
    • For examples of transition metal-mediated cycloaddition approaches toward five-membered ring-formation, see: (a) Herndon, J. W. J. Am. Chem. Soc. 1987, 109, 3165.
    • (1987) J. Am. Chem. Soc. , vol.109 , pp. 3165
    • Herndon, J.W.1
  • 9
    • 0002307453 scopus 로고
    • (g) For a review of Pauson-Khand reaction, see: Schore, N. E. Org. React. 1991, 40, 1.
    • (1991) Org. React. , vol.40 , pp. 1
    • Schore, N.E.1
  • 22
    • 0000154977 scopus 로고
    • Trost, B. M., Ed.; Pergamon Press: Oxford
    • (b) Ohta, T.; Takaya, H. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 5, p 1185.
    • (1991) Comprehensive Organic Synthesis , vol.5 , pp. 1185
    • Ohta, T.1    Takaya, H.2
  • 24
  • 41
    • 0001056196 scopus 로고
    • For a full account of the intramolecular cycloadditions with bifunctional conjunctive reasents, see: Trost, B. M.; Grese, T. A.; Chan, D. M. T. J. Am. Chem. Soc. 1991, 113, 7350.
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 7350
    • Trost, B.M.1    Grese, T.A.2    Chan, D.M.T.3
  • 75
    • 33646962736 scopus 로고    scopus 로고
    • note
    • Binger found that ligands such as maleic anhydride, acrolein, and acrylonitrile which bind very tightly to the catalyst can prevent any interaction of the metal with MCP, and thus inhibit the cycloaddition. See ref 3a.
  • 76
    • 33646951900 scopus 로고    scopus 로고
    • note
    • Binger found that intermolecular cycloaddition of MCP with simple unstrained alkenes is complicated by cyclodimerization of MCP rather than codimerization of MCP with alkenes due to the fact that MCP competes successfully with unactivated alkenes in π-complexation to the metal. This drawback can be overcome by simply using MCP substituted at the vinylic position to decrease the degree of π-complexation to the metal. See ref 3a.
  • 77
    • 33646963347 scopus 로고
    • TMM-metal complexes from metal-induced disrotatory ring openins of alkylidenecyclopropanes are known. For the iron complex, see: (a) Noyori, R.; Nishimura, T.; Takaya, H. J. Chem. Soc. D. 1969, 80.
    • (1969) J. Chem. Soc. D. , pp. 80
    • Noyori, R.1    Nishimura, T.2    Takaya, H.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.