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Volumn 75, Issue 15, 2010, Pages 5414-5416

An alkynyliodide cycloaddition strategy for the construction of iodoisoxazoles

Author keywords

[No Author keywords available]

Indexed keywords

FUNCTIONALIZATIONS; IODOALKYNES; NITRILE OXIDES; SUZUKI CROSS COUPLING;

EID: 77955153988     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo1011174     Document Type: Article
Times cited : (67)

References (36)
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    • De Meijere A.; Diederich F. Wiley-VCH: Weinheim, Germany
    • Metal-Catalyzed Cross-Coupling Reactions II; de Meijere, A. and Diederich, F., Eds.; Wiley-VCH: Weinheim, Germany, 2004.
    • (2004) Metal-Catalyzed Cross-Coupling Reactions II
  • 2
    • 30144445489 scopus 로고    scopus 로고
    • For examples of metal-mediated cycloadditions of alkynyliodides, see
    • For examples of metal-mediated cycloadditions of alkynyliodides, see: Yoo, W.-J.; Allen, A.; Villeneuve, K.; Tam, W. Org. Lett. 2005, 7, 5853
    • (2005) Org. Lett. , vol.7 , pp. 5853
    • Yoo, W.-J.1    Allen, A.2    Villeneuve, K.3    Tam, W.4
  • 7
    • 77955170036 scopus 로고    scopus 로고
    • Giomi D.; Cordero F.M.; Machetti F.; Katritzky A.R.; Ramsden C.A.; Scriven E.F.V.; Taylor R.J.K. Elsevier: Oxford
    • Giomi, D.; Cordero, F. M.; Machetti, F. In Comprehensive Heterocyclic Chemistry III; Katritzky, A. R.; Ramsden, C. A.; Scriven, E. F. V.; Taylor, R. J. K., Eds.; Elsevier: Oxford, 2008; Vol. 4, p 365.
    • (2008) Comprehensive Heterocyclic Chemistry III , vol.4 , pp. 365
  • 8
    • 0346690014 scopus 로고    scopus 로고
    • For a variety of recent methods for the preparation of isoxazoles, see
    • For a variety of recent methods for the preparation of isoxazoles, see: Sheng, S.-R.; Liu, X.-L.; Xu, Q.; Song, C.-U. Synthesis 2003, 2763
    • (2003) Synthesis , pp. 2763
    • Sheng, S.-R.1    Liu, X.-L.2    Xu, Q.3    Song, C.-U.4
  • 25
    • 77955168549 scopus 로고    scopus 로고
    • NOE analysis of the product provided no evidence for the interaction of the hydrogens of the phenyl ring with those of the mesityl group; see the Supporting Information
    • NOE analysis of the product provided no evidence for the interaction of the hydrogens of the phenyl ring with those of the mesityl group; see the Supporting Information.
  • 26
    • 0025802764 scopus 로고
    • We were aware that lithiation of a 5-iodoisoxazole isomer may well result in ring decomposition.;;;, However, given the yield and purity of crude products 4 and 22, we believe that this implies excellent regioselectivity in the preceeding cycloaddition
    • We were aware that lithiation of a 5-iodoisoxazole isomer may well result in ring decomposition. Sakamoto, T.; Kondo, Y.; Uchiyama, D.; Yamanaka, H. Tetrahedron 1991, 47, 5111 However, given the yield and purity of crude products 4 and 22, we believe that this implies excellent regioselectivity in the preceeding cycloaddition.
    • (1991) Tetrahedron , vol.47 , pp. 5111
    • Sakamoto, T.1    Kondo, Y.2    Uchiyama, D.3    Yamanaka, H.4
  • 27
    • 77955140173 scopus 로고    scopus 로고
    • 1H NMR spectra of some of the products contain a <5% impurity, which could not be separated and characterized but may be a minor regioisomer
    • 1H NMR spectra of some of the products contain a <5% impurity, which could not be separated and characterized but may be a minor regioisomer.
  • 28
    • 12344285900 scopus 로고    scopus 로고
    • For some examples of palladium-catalyzed cross-coupling of 4-haloisoxazoles, see
    • For some examples of palladium-catalyzed cross-coupling of 4-haloisoxazoles, see: Sahoo, A. K.; Oda, T.; Nakao, Y.; Hiyama, T. Adv. Synth. Catal. 2004, 346, 1715
    • (2004) Adv. Synth. Catal. , vol.346 , pp. 1715
    • Sahoo, A.K.1    Oda, T.2    Nakao, Y.3    Hiyama, T.4
  • 36
    • 0003942864 scopus 로고
    • We believe that the regioselectivity is determined by steric effects. For a list of appropriate "A-Values", see:;;;, Eds.; Wiley-Interscience: New York,; pp - 697
    • We believe that the regioselectivity is determined by steric effects. For a list of appropriate "A-Values", see: Stereochemistry of Organic Compounds; Eliel, E. L.; Wilen, S. H.; Mander, L. N., Eds.; Wiley-Interscience: New York, 1994; pp 696 - 697.
    • (1994) Stereochemistry of Organic Compounds , pp. 696
    • Eliel, E.L.1    Wilen, S.H.2    Mander, L.N.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.