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Volumn 47, Issue 43, 2008, Pages 8255-8258

An efficient approach to substituted 1,5,7,8,9-pentahydrocyclopenta-[h]-2- benzopyran-3-one derivatives by a palladium-catalyzed tandem reaction of 2,7-alkadiynylic carbonates with 2,3-allenoic acids

Author keywords

Allenoic acids; Cyclization; Palladium; Tandem reactions

Indexed keywords

ACIDS; CHEMICAL REACTIONS; CYCLIZATION; KETONES;

EID: 54249138096     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200803424     Document Type: Article
Times cited : (21)

References (70)
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    • a) S. Ma in Topics in Organometallic Chemistry (Ed.: J. Tsuji), Springer, Heidelberg, 2005, pp. 183-210;
    • (2005) Topics in Organometallic Chemistry , pp. 183-210
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    • b) The Chemistry of the Allenes, Vol. 1 (Ed.: S. R. Landor), Academic Press, London, 1982;
    • (1982) The Chemistry of the Allenes , vol.1
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    • Modern Allene Chemistry, Vols. 1 and 2 (Eds.: N. Krause, A. S. K. Hashmi), Wiley-VCH, Weinheim, 2004;
    • c) Modern Allene Chemistry, Vols. 1 and 2 (Eds.: N. Krause, A. S. K. Hashmi), Wiley-VCH, Weinheim, 2004;
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    • 34248345141 scopus 로고    scopus 로고
    • For selected reports from our research group, see: a
    • For selected reports from our research group, see: a) F. Yu, X. Lian, S. Ma, Org. Lett. 2007, 9, 1703;
    • (2007) Org. Lett , vol.9 , pp. 1703
    • Yu, F.1    Lian, X.2    Ma, S.3
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    • 54249108627 scopus 로고    scopus 로고
    • For a palladium(II)-catalyzed cyclization of 2,3-allenoic acids in the presence of propargylic carbonates to afford β-allenyl butenolides, see: S. Ma, Z. Gu, Y. Deng, Chem. Commun. 2006, 94.
    • For a palladium(II)-catalyzed cyclization of 2,3-allenoic acids in the presence of propargylic carbonates to afford β-allenyl butenolides, see: S. Ma, Z. Gu, Y. Deng, Chem. Commun. 2006, 94.
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    • For the cyclic carbopalladation and coupling reaction of 2,7-alkadiynylic carbonates with typical organometallic reagents, see: a
    • For the cyclic carbopalladation and coupling reaction of 2,7-alkadiynylic carbonates with typical organometallic reagents, see: a) J. Tsuji, T. Mandai, Angew. Chem. 1995, 107, 2830;
    • (1995) Angew. Chem , vol.107 , pp. 2830
    • Tsuji, J.1    Mandai, T.2
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    • Crystal data for 3a: Recrystallization from acetone/diethyl ether (1:10, C23H27NO4S, MW=413.52, Monoclinic, space group P21/c, MoK, final R indices [I>2σ(I, R1=0.0633, wR2=0.1486, R indices (all data, R1=0.0963, wR2=0.1647; a=12.6156(17) Å, b=7.5890(11) Å, c=23.006(3) Å, α=90, β=100.518(3, γ=90°, V=2165.6(5) Å3, T=293(2) K, wavelength: 0.71073 Å, Z=4, reflections collected/unique 12125/4704 (Rint=0.1281, number of observation [I>2sI, 2980, parameters 268. CCDC 675814 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via
    • int=0.1281), number of observation [I>2s(I)] 2980, parameters 268. CCDC 675814 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
  • 57
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    • For reports of the kinetic resolution of propargylic alcohols, see: a
    • For reports of the kinetic resolution of propargylic alcohols, see: a) P. Allevi, P. Ciuffreda, M. Anastasia, Tetrahedron: Asymmetry 1997, 8 93;
    • (1997) Tetrahedron: Asymmetry , vol.8 , pp. 93
    • Allevi, P.1    Ciuffreda, P.2    Anastasia, M.3
  • 59
    • 54249165627 scopus 로고    scopus 로고
    • Crystal data for 4b: Recrystallization from acetone/diethyl ether (1:10, C29H30BrNO4S, MW=568.51, Monoclinic, space group P21/n, MoK, final R indices [I>2σ(I, R1=0.0424, wR2=0.0778, R indices (all data, R1=0.0984, wR2=0.0868; a=17.4190(17) Å, b=9.6103(10) Å, c=31.794(3) Å, α=90°, β=93.815(2)°, γ=90°, V=5310.5(9) Å3, T=293(2) K, wavelength: 0.71073 Å, Z=8, reflections collected/unique 27183/9845 (Rint=0.0900, number of observation [I>2σI, 4485, parameters 657. CCDC 675815 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via
    • int=0.0900), number of observation [I>2σ(I)] 4485, parameters 657. CCDC 675815 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.