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Volumn 126, Issue 34, 2004, Pages 10540-10541

Nickel-catalyzed intermolecular [3 + 2 + 2] cocyclization of ethyl cyclopropylideneacetate and alkynes

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID DERIVATIVE; ALKYNE DERIVATIVE; ETHYL CYCLOPROPYLIDENEACETATE; NICKEL; UNCLASSIFIED DRUG;

EID: 4344715554     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0494306     Document Type: Article
Times cited : (121)

References (41)
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    • For the transition metal-catalyzed [4 + 3] cycloaddition reactions, see: (a) Binger, P.; Büch, H. M. Top. Curr. Chem. 1987, 135, 77-151.
    • (1987) Top. Curr. Chem. , vol.135 , pp. 77-151
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  • 8
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    • The nickel-catalyzed reaction of methylenecyclopropane with allene and the cyclotrimerization of methylenecyclopropane have been reported. See: (a) Binger, P.; McMeeking, J. Angew. Chem. 1973, 85, 1053-1054.
    • (1973) Angew. Chem. , vol.85 , pp. 1053-1054
    • Binger, P.1    McMeeking, J.2
  • 11
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    • For the transition metal-mediated [3 + 2 + 2] cycloaddition reactions, see: (a) Schwiebert, K. E.; Stryker, J. M. J. Am. Chem. Soc. 1995, 117, 8275-8276.
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 8275-8276
    • Schwiebert, K.E.1    Stryker, J.M.2
  • 21
    • 0347812067 scopus 로고    scopus 로고
    • Palladium-Catalyzed beniannulation reactions of enynes and diynes
    • Negishi, E.-i., de Meijere, A., Eds.; Wiley: New York
    • (d) Saito, S.; Yamamoto, Y. Palladium-Catalyzed Beniannulation Reactions of Enynes and Diynes. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E.-i., de Meijere, A., Eds.; Wiley: New York, 2002; pp 1635-1646.
    • (2002) Handbook of Organopalladium Chemistry for Organic Synthesis , pp. 1635-1646
    • Saito, S.1    Yamamoto, Y.2
  • 24
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    • note
    • This reaction also proceeded in THF (65% yield). The yield of 2a decreased when this reaction was carried out at 0 °C (56%) or 50 °C (59%). The reaction of 1 with 2a was carried out in a larger scale (15 mmol scale) without difficulty: 3a was isolated in 72% yield. The major byproducts of these reactions were cyclopentanes which were formed by the cyclodimerization of 1 and the oligomers of 2.
  • 25
    • 4344657167 scopus 로고    scopus 로고
    • note
    • The progress of the reaction was very slow, and the starting material did not disappear even after the prolonged monitoring of the reaction.
  • 29
    • 0000134376 scopus 로고
    • Transition metal alkyne complexes: Transition metal-catalyzed cyclotrimerization
    • Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Hegedus, L. S., Vol. Ed.; Pergamon Press: Oxford
    • Reviews: (a) Grotjahn, D. B. Transition Metal Alkyne Complexes: Transition Metal-Catalyzed Cyclotrimerization. In Comprehensive Organometallic Chemistry 11; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Hegedus, L. S., Vol. Ed.; Pergamon Press: Oxford, 1995; Vol. 12, pp 741-770.
    • (1995) Comprehensive Organometallic Chemistry 11 , vol.12 , pp. 741-770
    • Grotjahn, D.B.1
  • 30
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    • Nickel catalyzed oligomerization of alkynes and related reactions
    • Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: Oxford
    • (b) Jolly, P. W. Nickel Catalyzed Oligomerization of Alkynes and Related Reactions. In Comprehensive. Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: Oxford, 1982; Vol. 8, pp 649-670.
    • (1982) Comprehensive. Organometallic Chemistry , vol.8 , pp. 649-670
    • Jolly, P.W.1
  • 34
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    • The isolation of a closely related intermediate and its rearrangement has been reported. See, Binger, P.; Doyle, M. J.; Benn, R. Chem. Ber. 1983, 116, 1-10.
    • (1983) Chem. Ber. , vol.116 , pp. 1-10
    • Binger, P.1    Doyle, M.J.2    Benn, R.3
  • 35
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    • Cleavage of carbon-carbon single bonds by transition metals
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    • For the leading references, see: (a) Murakami, M.; Ito, Y. Cleavage of Carbon-Carbon Single Bonds by Transition Metals. In Activation of Unreactive Bonds and Organic Synthesis; Murai, S., Ed.; Springer: Berlin, 1999; pp 97-129.
    • (1999) Activation of Unreactive Bonds and Organic Synthesis , pp. 97-129
    • Murakami, M.1    Ito, Y.2
  • 39
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    • The insertion of a nickel complex into a strained σ bond has been reported in some reactions. For example, see: (a) Neidlein, V.; Rufinska, A.; Schwager, H.; Wilke, G. Angew. Chem. 1986, 98, 643-644.
    • (1986) Angew. Chem. , vol.98 , pp. 643-644
    • Neidlein, V.1    Rufinska, A.2    Schwager, H.3    Wilke, G.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.