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Volumn 75, Issue 2, 2010, Pages 480-483

Nickel-catalyzed [3+2+2] cycloaddition of ethyl cyclopropylideneacetate and heteroatom-substituted alkynes: Application to selective three-component reaction with 1,3-diynes

Author keywords

[No Author keywords available]

Indexed keywords

[2 + 2] CYCLOADDITION; CHEMICAL EQUATIONS; EFFICIENT METHOD; HETEROATOMS; RELATED COMPOUNDS; THREE COMPONENT REACTIONS; THREE-COMPONENT;

EID: 75349095927     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo902251m     Document Type: Article
Times cited : (59)

References (33)
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  • 2
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    • and references cited therein
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  • 3
    • 0033855773 scopus 로고    scopus 로고
    • For reviews on Ni-catalyzed multicomponent reactions, see: a
    • For reviews on Ni-catalyzed multicomponent reactions, see: (a) Ikeda, S.-i. Acc. Chem. Res. 2000, 33, 511-519.
    • (2000) Acc. Chem. Res , vol.33 , pp. 511-519
    • Ikeda, S.-I.1
  • 14
    • 33751518128 scopus 로고    scopus 로고
    • For a review of the reaction of ynolate and ynol ether, see
    • For a review of the reaction of ynolate and ynol ether, see: Shindo, M. Tetrahedron 2007, 63, 10-36.
    • (2007) Tetrahedron , vol.63 , pp. 10-36
    • Shindo, M.1
  • 15
    • 0000130007 scopus 로고
    • For reviews of the reaction of ynamine and ynamide, see: a
    • For reviews of the reaction of ynamine and ynamide, see: (a) Ficini, J. Tetrahedron 1976, 32, 1449-1486.
    • (1976) Tetrahedron , vol.32 , pp. 1449-1486
    • Ficini, J.1
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    • For representative examples of the reactions of ynol ether in the presence of transition metals, see: a
    • For representative examples of the reactions of ynol ether in the presence of transition metals, see: (a) Castro, J.; Sörensen, H.; Riera, A.; Morin, C.; Moyano, A.; Pericàs, M. A.; Greene, A. E. J. Am. Chem. Soc. 1990, 112, 9388-9389.
    • (1990) J. Am. Chem. Soc , vol.112 , pp. 9388-9389
    • Castro, J.1    Sörensen, H.2    Riera, A.3    Morin, C.4    Moyano, A.5    Pericàs, M.A.6    Greene, A.E.7
  • 21
    • 0006933444 scopus 로고
    • For typical examples of the reaction of ynamine or ynamide with transition metal, see: a
    • For typical examples of the reaction of ynamine or ynamide with transition metal, see: (a) Ficini, J.; d'Angelo, J.; Falou, S. Tetrahedron Lett. 1977, 19, 1645-1648.
    • (1977) Tetrahedron Lett , vol.19 , pp. 1645-1648
    • Ficini, J.1    d'Angelo, J.2    Falou, S.3
  • 29
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    • 1H NMR spectra according to previous results (see refs 3a, 3b, and 3e). The high E-selectivity was determined at the stage of rearrangement that prefers the s-trans conformation of the C(carbonyl)-C(α)-C(β)-C(γ) bond (see ref 3e).
    • 1H NMR spectra according to previous results (see refs 3a, 3b, and 3e). The high E-selectivity was determined at the stage of rearrangement that prefers the s-trans conformation of the C(carbonyl)-C(α)-C(β)-C(γ) bond (see ref 3e).
  • 30
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    • The yield of the product decreased since the isolation of the product from the byproducts turned out to be difficult
    • The yield of the product decreased since the isolation of the product from the byproducts turned out to be difficult.
  • 33
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    • Cheng et al. reported the alkyne moiety bound to a more bulky group was more reactive. The difference probably stemmed from the sequence of cocyclization. In their proposed reaction mechanism, the 1,3-diyne was inserted into metallacycle, in our case being a component metallacycle. See: Jeevanandam, A.; Prasad, R.; Huang, K. I.-w.; Cheng, C.-H. Org. Lett. 2002, 4, 807-810.
    • Cheng et al. reported the alkyne moiety bound to a more bulky group was more reactive. The difference probably stemmed from the sequence of cocyclization. In their proposed reaction mechanism, the 1,3-diyne was inserted into metallacycle, in our case being a component metallacycle. See: Jeevanandam, A.; Prasad, R.; Huang, K. I.-w.; Cheng, C.-H. Org. Lett. 2002, 4, 807-810.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.