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Volumn 349, Issue 16, 2007, Pages 2493-2498

Gold-catalyzed tandem cycloisomerization of alkynyloxiranes with nucleophiles: An efficient approach to 2,5-disubstituted furans

Author keywords

Alkynes; Alkynyloxiranes; Cycloisomerization; Epoxides; Furans; Gold

Indexed keywords


EID: 36749091693     PISSN: 16154150     EISSN: 15213897     Source Type: Journal    
DOI: 10.1002/adsc.200700319     Document Type: Article
Times cited : (85)

References (63)
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    • Recent reviews: a) X. L. Hou, Z. Yang, H. N. C. Wong, in : Progress in Heterocyclic Chemistry, (Eds. : G. W. Gribble, T. L. Gilchrist), Pergamon, Oxford, 2002, Vol. 14, pp 139-179;
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    • synlanti mixtures of the substrate esters of 1-alkynyl-2,3-epoxy alcohols were used. The reaction products were not found to be affected by the stereochemical configuration of the substrate. For a full explanation and definition of the terms syn and anti as used herein see: C. M. Marson, D. W. M. Benzies, A.D. Hobson, Tetrahedron 1991, 47, 5491-5506.
    • synlanti mixtures of the substrate esters of 1-alkynyl-2,3-epoxy alcohols were used. The reaction products were not found to be affected by the stereochemical configuration of the substrate. For a full explanation and definition of the terms syn and anti as used herein see: C. M. Marson, D. W. M. Benzies, A.D. Hobson, Tetrahedron 1991, 47, 5491-5506.
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    • The substrate bearing a propargyl acetate functionality might undergo a 1,3-migration to form the corresponding products, a common reaction pathway of propargyl carboxylates. See: N. Marion, S. P. Nolan, Angew. Chem. Int. Ed. 2007, 46, 2750-2752, and references cited therein.
    • The substrate bearing a propargyl acetate functionality might undergo a 1,3-migration to form the corresponding products, a common reaction pathway of propargyl carboxylates. See: N. Marion, S. P. Nolan, Angew. Chem. Int. Ed. 2007, 46, 2750-2752, and references cited therein.
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    • Based on simpler and inexpensive gold species, HAuCl4-4H20 was employed as the catalyst for many transformations.
    • Based on simpler and inexpensive gold species, HAuCl4-4H20 was employed as the catalyst for many transformations.
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    • 4] is an efficient gold catalyst in the synthesis of highly substituted furans. See: X. Liu, Z. Pan, X. Shu, X. Duan, Y. Liang, Synlett 2006, 1962-1964.
    • 4] is an efficient gold catalyst in the synthesis of highly substituted furans. See: X. Liu, Z. Pan, X. Shu, X. Duan, Y. Liang, Synlett 2006, 1962-1964.
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    • [4f,h]
    • [4f,h]
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    • Similar intermediate have been reported by Sarpong, see : a B. G. Pujanauski, B. A. Bhanu Prasad, R. Sarpong, J. Am. Chem. Soc. 2006, 128, 6786-6787. For the transition metal-catalyzed oxonium ion formation, see:
    • Similar intermediate have been reported by Sarpong, see : a) B. G. Pujanauski, B. A. Bhanu Prasad, R. Sarpong, J. Am. Chem. Soc. 2006, 128, 6786-6787. For the transition metal-catalyzed oxonium ion formation, see:
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    • A similar mechanism has been reported by Marson, see
    • A similar mechanism has been reported by Marson, see: C. M. Marson, J. Campbell, Tetrahedron Lett. 1997, 38, 7785-7788.
    • (1997) Tetrahedron Lett , vol.38 , pp. 7785-7788
    • Marson, C.M.1    Campbell, J.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.