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Volumn 40, Issue 51, 1999, Pages 8949-8953

Vinylogous Mannich reactions. Catalytic, asymmetric additions of triisopropylsilyloxyfurans to aldimines

Author keywords

Asymmetric reactions; Catalysis; Furanones; Imines

Indexed keywords

BUTENOLIDE; FURANONE DERIVATIVE; IMINE; TITANIUM DERIVATIVE;

EID: 0033579639     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01939-5     Document Type: Article
Times cited : (78)

References (30)
  • 1
    • 0029034764 scopus 로고
    • For a review of reactions of trialkylsilyloxyfurans, see: (a) Casiraghi, G.; Rassu, G. Synthesis 1995, 607-626.
    • (1995) Synthesis , pp. 607-626
    • Casiraghi, G.1    Rassu, G.2
  • 4
    • 0026572247 scopus 로고
    • (b) Martin, S. F.; Corbett, J. W. Synthesis 1992, 55-57. (c) Morimoto, Y.; Nishida, K.; Hayashi, Y. Tetrahedron Lett. 1993, 34, 5773-5776.
    • (1992) Synthesis , pp. 55-57
    • Martin, S.F.1    Corbett, J.W.2
  • 9
    • 0027130840 scopus 로고
    • For applications of vinylogous Mannich reactions to alkaloid synthesis, see: (a) Martin, S. F.; Liras, S. J. Am. Chem. Soc. 1993, 115, 10450-10451.
    • (1993) J. Am. Chem. Soc. , vol.115 , pp. 10450-10451
    • Martin, S.F.1    Liras, S.2
  • 20
    • 0038475549 scopus 로고    scopus 로고
    • For examples of catalytic, vinylogous Mukaiyama-type reactions, see: (a) Kruger, J.; Carierra, E. M. J. Am. Chem. Soc. 1998, 120, 837-838.
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 837-838
    • Kruger, J.1    Carierra, E.M.2
  • 23
    • 0000862669 scopus 로고    scopus 로고
    • For a review of catalytic, enantioselective additions to imines, see: Kobayashi, S.; Ishitani, H. Chem. Rev. 1999, 99, 1069-1094.
    • (1999) Chem. Rev. , vol.99 , pp. 1069-1094
    • Kobayashi, S.1    Ishitani, H.2
  • 24
    • 85038144312 scopus 로고    scopus 로고
    • note
    • 13C NMR, IR, MS) characteristics. Analytical samples of all new compounds were obtained by distillation, recrystallization, or preparative HPLC or TLC and gave satisfactory combustion analysis (C,H) and/or identification by high-resolution mass spectrometry. All yields are based on isolated, purified materials.
  • 30
    • 85038143169 scopus 로고    scopus 로고
    • note
    • 4) and concentrated, and the resulting residue was purified by flash chromatography eluting with hexanes:EtOAc (70:30) to yield the adduct. The (5)-BINOL can be recovered.


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