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Volumn 58, Issue 7, 1993, Pages 1835-1839

New Effective Catalysts for Mukaiyama-Aldol and -Michael Reactions: BiCl3-Metallic Iodide Systems

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EID: 0001253387     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00059a040     Document Type: Article
Times cited : (105)

References (48)
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    • Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York
    • Heathcock, C. H. In The Aldol Addition Reaction in Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1984; Vol. 3, p 111;
    • (1984) The Aldol Addition Reaction , vol.3 , pp. 111
    • Heathcock, C.H.1
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    • Tetrahedron 1983, 39, 117.
    • (1983) Tetrahedron , vol.39 , pp. 117
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    • Combinations of tin(II) chloride or triflate with neutral molecule or Lewis acid
    • Combinations of tin(II) chloride or triflate with neutral molecule or Lewis acid: Iwasawa, N.; Mukaiyama, T. Chem. Lett. 1987, 463.
    • (1987) Chem. Lett. , pp. 463
    • Iwasawa, N.1    Mukaiyama, T.2
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  • 39
    • 0001118685 scopus 로고
    • The mechanism of the catalyzed Mukaiyama-Aldol and -Michael reactions are not definitively established. It seems generally accepted that aldol-type reactions in aprotic solvents occur through enolates possessing a Lewis acidic metal counterion via a six-membered chelate transition state (ref 6a and references cited therein). The intervention of Lewis acid mediated electron transfer in the Mukaiyama-Michael reaction has been recently suggested, and references cited therein
    • The mechanism of the catalyzed Mukaiyama-Aldol and -Michael reactions are not definitively established. It seems generally accepted that aldol-type reactions in aprotic solvents occur through enolates possessing a Lewis acidic metal counterion via a six-membered chelate transition state (ref 6a and references cited therein). The intervention of Lewis acid mediated electron transfer in the Mukaiyama-Michael reaction has been recently suggested: Sato, T.; Wakahara, Y.; Otera, J.; Nozaki, H. J. Am. Chem. Soc. 1991, 113, 4028 and references cited therein.
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 4028
    • Sato, T.1    Wakahara, Y.2    Otera, J.3    Nozaki, H.4
  • 40
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    • (pp 2227–9) and references cited therein
    • Olah, G. A.; Narang, S. C. Tetrahedron 1982, 38, 2225 (pp 2227–9) and references cited therein.
    • (1982) Tetrahedron , vol.38 , pp. 2225
    • Olah, G.A.1    Narang, S.C.2
  • 42
    • 37049089571 scopus 로고
    • For the chemistry of β-(silylozy) carbonyl compounds, see
    • For the chemistry of β-(silylozy) carbonyl compounds, see: (a) Anwar, S.; Davis, A. P. J. Chem. Soc., Chem. Commun. 1986, 831;
    • (1986) J. Chem. Soc., Chem. Commun. , pp. 831
    • Anwar, S.1    Davis, A.P.2
  • 43
    • 0001500070 scopus 로고
    • Tetrahedron 1988, 44, 3761.
    • (1988) Tetrahedron , vol.44 , pp. 3761


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