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Volumn 44, Issue 22, 2003, Pages 4171-4174

InBr3-Et3N promoted alkynylation of aldehydes and N,O-acetals under mild conditions: Facile and simple preparation of propargylic alcohols and amines

Author keywords

Alkynylation; Indium tribromide; N,O acetal; Propargylic alcohol; Propargylic amine

Indexed keywords

ACETAL DERIVATIVE; ALCOHOL DERIVATIVE; ALKYNE; AMINE; INDIUM; REAGENT;

EID: 0038739256     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)00931-6     Document Type: Article
Times cited : (60)

References (32)
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    • Yamamoto, H., Ed.; Wiley-VCH: Weinheim
    • For selected reviews and papers for indium-promoted or catalyzed reactions, see: (a) Marshall, J. A. In Lewis Acids in Organic Synthesis, Yamamoto, H., Ed.; Wiley-VCH: Weinheim, 2000; Vol. 1, p. 453; (b) Onishi, Y.; Ito, T.; Yasuda, M.; Baba, A. Eur. J. Org. Chem. 2002, 1578; (c) Chauhan, K. K.; Frost, C. G. J. Chem. Soc., Perkin Trans. 1 2000, 3015; (d) Ranu, B. C. Eur. J. Org. Chem. 2000, 2347; (e) Marshall, J. A.; Hinkle, K. W. J. Org. Chem. 1995, 60, 1920.
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    • For selected reviews and papers for indium-promoted or catalyzed reactions, see: (a) Marshall, J. A. In Lewis Acids in Organic Synthesis, Yamamoto, H., Ed.; Wiley-VCH: Weinheim, 2000; Vol. 1, p. 453; (b) Onishi, Y.; Ito, T.; Yasuda, M.; Baba, A. Eur. J. Org. Chem. 2002, 1578; (c) Chauhan, K. K.; Frost, C. G. J. Chem. Soc., Perkin Trans. 1 2000, 3015; (d) Ranu, B. C. Eur. J. Org. Chem. 2000, 2347; (e) Marshall, J. A.; Hinkle, K. W. J. Org. Chem. 1995, 60, 1920.
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    • For selected reviews and papers for indium-promoted or catalyzed reactions, see: (a) Marshall, J. A. In Lewis Acids in Organic Synthesis, Yamamoto, H., Ed.; Wiley-VCH: Weinheim, 2000; Vol. 1, p. 453; (b) Onishi, Y.; Ito, T.; Yasuda, M.; Baba, A. Eur. J. Org. Chem. 2002, 1578; (c) Chauhan, K. K.; Frost, C. G. J. Chem. Soc., Perkin Trans. 1 2000, 3015; (d) Ranu, B. C. Eur. J. Org. Chem. 2000, 2347; (e) Marshall, J. A.; Hinkle, K. W. J. Org. Chem. 1995, 60, 1920.
    • (2000) J. Chem. Soc., Perkin Trans. 1 , pp. 3015
    • Chauhan, K.K.1    Frost, C.G.2
  • 16
    • 0033928629 scopus 로고    scopus 로고
    • For selected reviews and papers for indium-promoted or catalyzed reactions, see: (a) Marshall, J. A. In Lewis Acids in Organic Synthesis, Yamamoto, H., Ed.; Wiley-VCH: Weinheim, 2000; Vol. 1, p. 453; (b) Onishi, Y.; Ito, T.; Yasuda, M.; Baba, A. Eur. J. Org. Chem. 2002, 1578; (c) Chauhan, K. K.; Frost, C. G. J. Chem. Soc., Perkin Trans. 1 2000, 3015; (d) Ranu, B. C. Eur. J. Org. Chem. 2000, 2347; (e) Marshall, J. A.; Hinkle, K. W. J. Org. Chem. 1995, 60, 1920.
    • (2000) Eur. J. Org. Chem. , pp. 2347
    • Ranu, B.C.1
  • 17
    • 0000544750 scopus 로고
    • For selected reviews and papers for indium-promoted or catalyzed reactions, see: (a) Marshall, J. A. In Lewis Acids in Organic Synthesis, Yamamoto, H., Ed.; Wiley-VCH: Weinheim, 2000; Vol. 1, p. 453; (b) Onishi, Y.; Ito, T.; Yasuda, M.; Baba, A. Eur. J. Org. Chem. 2002, 1578; (c) Chauhan, K. K.; Frost, C. G. J. Chem. Soc., Perkin Trans. 1 2000, 3015; (d) Ranu, B. C. Eur. J. Org. Chem. 2000, 2347; (e) Marshall, J. A.; Hinkle, K. W. J. Org. Chem. 1995, 60, 1920.
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    • Baba et al. have already reported that the smooth reaction of indium acetylides, which are generated by transmetalation between alkynyl tins and indium chloride, with aldehydes. See:
    • Baba et al. have already reported that the smooth reaction of indium acetylides, which are generated by transmetalation between alkynyl tins and indium chloride, with aldehydes. See: Yasuda M., Miyai T., Shibata I., Baba A., Nomura R., Matsuda H. Tetrahedron Lett. 36:1995;9497.
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    • note
    • 29N: 271.2300. Found: 271.2302.
  • 29
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    • A few papers dealing with the preparation of propargylic amines using alkynyl metals and N,O-acetals have been reported, see: (a) Fleming, J. J.; Flori, K. W.; Du Bois, J. J. Am. Chem. Soc. 2003, 125, 2028; (b) Barluenga, J.; Campos, P. J.; Canal, G. Synthesis 1989, 33; (c) Mensnard, D.; Miginiac, L. J. Organomet. Chem. 1989, 373, 1; (c) Courtois, G.; Miginiac, P. Bull. Soc. Chim. Fr. 1983, 1-2, 21.
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 2028
    • Fleming, J.J.1    Flori, K.W.2    Du Bois, J.3
  • 30
    • 84914329569 scopus 로고
    • A few papers dealing with the preparation of propargylic amines using alkynyl metals and N,O-acetals have been reported, see: (a) Fleming, J. J.; Flori, K. W.; Du Bois, J. J. Am. Chem. Soc. 2003, 125, 2028; (b) Barluenga, J.; Campos, P. J.; Canal, G. Synthesis 1989, 33; (c) Mensnard, D.; Miginiac, L. J. Organomet. Chem. 1989, 373, 1; (c) Courtois, G.; Miginiac, P. Bull. Soc. Chim. Fr. 1983, 1-2, 21.
    • (1989) Synthesis , pp. 33
    • Barluenga, J.1    Campos, P.J.2    Canal, G.3
  • 31
    • 0001819767 scopus 로고
    • A few papers dealing with the preparation of propargylic amines using alkynyl metals and N,O-acetals have been reported, see: (a) Fleming, J. J.; Flori, K. W.; Du Bois, J. J. Am. Chem. Soc. 2003, 125, 2028; (b) Barluenga, J.; Campos, P. J.; Canal, G. Synthesis 1989, 33; (c) Mensnard, D.; Miginiac, L. J. Organomet. Chem. 1989, 373, 1; (c) Courtois, G.; Miginiac, P. Bull. Soc. Chim. Fr. 1983, 1-2, 21.
    • (1989) J. Organomet. Chem. , vol.373 , pp. 1
    • Mensnard, D.1    Miginiac, L.2
  • 32
    • 0037466996 scopus 로고    scopus 로고
    • A few papers dealing with the preparation of propargylic amines using alkynyl metals and N,O-acetals have been reported, see: (a) Fleming, J. J.; Flori, K. W.; Du Bois, J. J. Am. Chem. Soc. 2003, 125, 2028; (b) Barluenga, J.; Campos, P. J.; Canal, G. Synthesis 1989, 33; (c) Mensnard, D.; Miginiac, L. J. Organomet. Chem. 1989, 373, 1; (c) Courtois, G.; Miginiac, P. Bull. Soc. Chim. Fr. 1983, 1-2, 21.
    • (1983) Bull. Soc. Chim. Fr. , vol.1-2 , pp. 21
    • Courtois, G.1    Miginiac, P.2


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