フルオラールを用いる含フッ素化合物の触媒的不斉合成  [in Japanese] Catalytic Asymmetric Synthesis of Organofluorine Compounds Using Fluoral  [in Japanese]

Access this Article

Search this Article

Author(s)

Abstract

Asymmetric synthesis of organofluorine compounds is an important issue in pharmaceutical chemistry and optoelectronic material science. In this respect, asymmetric catalysis of carboncarbon bond-forming reactions is the most attractive method. Asymmetric catalysis of ene, Mukaiyama-aldol and Friedel-Crafts reactions with fluoral is thus established using chiral binaphthol-derived titanium ((6-Br) -BINOL-Ti) catalysts to provide a practical synthetic route to the organofluorine compounds containing trifluoromethyl group.

Journal

  • Journal of Synthetic Organic Chemistry, Japan

    Journal of Synthetic Organic Chemistry, Japan 58(4), 324-333, 2000-04-01

    The Society of Synthetic Organic Chemistry, Japan

References:  97

  • <no title>

    OJIMA I.

    Biomedical Frontiers of Fluorine Chemistry, 1996

    Cited by (6)

  • <no title>

    RESNATI G.

    Symposia-in-Print 52(1), 1996

    Cited by (1)

  • <no title>

    FILLER R.

    Organofluorine Compounds in Medicinal Chemistry and Biomedical Applications, 1993

    Cited by (16)

  • <no title>

    SOLOSHONOK V. A.

    Enantiocontrolled Synthesis of Fluoro-organic Compounds, 1999

    Cited by (1)

  • <no title>

    山崎孝

    有合化 49, 721, 1991

    Cited by (5)

  • <no title>

    GREE R. L.

    Enantiocontrolled Synthesis of Fluoro-organic Compounds, 1999

    Cited by (1)

  • <no title>

    ISEKI K.

    Tetrahedron 53, 10271, 1997

    Cited by (2)

  • <no title>

    ISEKI K.

    Tetrahedron Lett. 37, 9081, 1996

    Cited by (1)

  • <no title>

    SOLOSHONOK V. A.

    Asymmetry 5, 1091, 1994

    Cited by (1)

  • <no title>

    MARUOKA K.

    Tetrahedron Lett. 29, 3967, 1988

    Cited by (3)

  • <no title>

    SOAI K.

    J. Fluorine Chem. 59, 5, 1992

    Cited by (3)

  • <no title>

    石井章央

    有合化 57, 898, 1999

    Cited by (1)

  • <no title>

    ISEKI K.

    Tetrahedron 52, 71, 1996

    Cited by (4)

  • <no title>

    MIKAMI K.

    Comprehensive Asymmetric Catalysis III, 1143, 1999

    Cited by (1)

  • <no title>

    MIKAMI K.

    Lewis Acid Reagents 93, 1999

    Cited by (1)

  • <no title>

    MIKAMI K.

    Pure and Appl. Chem. 68, 639, 1996

    Cited by (1)

  • <no title>

    MIKAMI K.

    Advances in Asymmetric Synthesis 1, 1, 1995

    Cited by (1)

  • <no title>

    MIKAMI K.

    Advances in Catalytic Processes 123, 1995

    Cited by (1)

  • <no title>

    MIKAMI K.

    Synlett 1992, 255

    Cited by (7)

  • <no title>

    MIKAMI K.

    Chem. Rev. 92, 1021, 1992

    Cited by (15)

  • <no title>

    MIKAMI K.

    Tetrahedron 52, 85, 1996

    Cited by (5)

  • <no title>

    MIKAMI K.

    Asymmetry 5, 1087, 1994

    Cited by (2)

  • <no title>

    MIKAMI K.

    Tetrahedron Lett. 34, 7591, 1993

    Cited by (4)

  • <no title>

    MIKAMI K.

    Synlett 1995, 1057

    Cited by (1)

  • <no title>

    ISHII A.

    J. Fluorine Chem. 97, 51, 1999

    Cited by (1)

  • <no title>

    ISHII A.

    Org. Lett. 1, 2013, 1999

    Cited by (1)

  • <no title>

    ISHII A.

    J. Org. Chem. 65, 1597, 2000

    Cited by (1)

  • <no title>

    PORAS H.

    Chem. Lett. 1998, 665

    Cited by (2)

  • <no title>

    MATSUTANI H.

    Chem. Commun. 1998, 1259

    Cited by (3)

  • <no title>

    IDEM.

    Synlett 1998, 1353

    Cited by (1)

  • <no title>

    WONG S. S.

    Chem. Commun. 1990, 456

    Cited by (1)

  • <no title>

    LINDERMAN R. J.

    J. Fluorine Chem. 53, 79, 1991

    Cited by (4)

  • <no title>

    REED A. E.

    J. Chem. Phys. 83, 735, 1985

    Cited by (11)

  • <no title>

    HOUK K. N.

    Science 231, 1108, 1986

    Cited by (12)

  • Stereoelectronic Rules in Addition Reactions: "Cram's Rule" in Olefinic Systems

    MIKAMI K.

    Advances in Detailed Reaction Mechanisms 3, 1993

    Cited by (1)

  • <no title>

    YAMAMOTO Y.

    Chem. Rev. 93, 2207, 1993

    Cited by (46)

  • <no title>

    永井隆文

    有合化 49, 624, 1991

    Cited by (1)

  • <no title>

    HEATHCOCK C. H.

    Asymmetric Synthesis 3, 1984

    Cited by (3)

  • <no title>

    EVANS D. A.

    Top. Stereochem. 1, 1982

    Cited by (1)

  • <no title>

    HEATHCOCK C. H.

    J. Org. Chem. 44, 4294, 1979

    Cited by (3)

  • <no title>

    NAGAI T.

    Chem. Pharm. Bull. 37, 177, 1989

    Cited by (1)

  • <no title>

    MIKAMI K.

    Tetrahedron Lett. 29, 6305, 1988

    Cited by (2)

  • <no title>

    HOUK K. N.

    J. Am. Chem. Soc. 103, 949, 1981

    Cited by (3)

  • <no title>

    SHULTE-ELTE K. H.

    J. Am. Chem. Soc. 102, 1738, 1980

    Cited by (1)

  • <no title>

    ORFANPOULOS M.

    J. Am. Chem. Soc. 101, 275, 1979

    Cited by (1)

  • <no title>

    MUKAIYAMA T.

    Org. React. 28, 203, 1982

    Cited by (13)

  • <no title>

    NELSON S. G.

    Asymmetry 9, 357, 1998

    Cited by (1)

  • <no title>

    GROGER H.

    Chem. Eur. J. 4, 1137, 1998

    Cited by (8)

  • <no title>

    BACH T.

    Int. Ed. Engl. 33, 417, 1994

    Cited by (1)

  • <no title>

    SMITH M. B.

    Organic Synthesis 1313, 1994

    Cited by (1)

  • <no title>

    HEANEY H.

    Comprehensive Organic Synthesis 2, 733, 1991

    Cited by (1)

  • <no title>

    ROBERTS R. M.

    Friedel-Crafts Alkylation Chemistry. A Century of Discovery, 1984

    Cited by (2)

  • <no title>

    OLAH G. A.

    Friedel-Crafts Chemistry, 1973

    Cited by (7)

  • <no title>

    COSTA P. R. R.

    Tetrahedron Lett. 38, 7021, 1997

    Cited by (1)

  • <no title>

    EL KAIM L.

    Tetrahedron Lett. 37, 375, 1996

    Cited by (1)

  • <no title>

    BIGI F.

    Tetrahedron: Asymmetry 4, 2411, 1993

    Cited by (1)

  • <no title>

    TERADA M.

    Synlett 1995, 411

    Cited by (1)

  • <no title>

    CASIRAGHI G.

    J. Org. Chem. 53, 1779, 1988

    Cited by (2)

  • <no title>

    ERKER G.

    Angew. Chem., Int. Ed. Engl. 29, 512, 1990

    Cited by (1)

  • <no title>

    BIGI F.

    J. Org. Chem. 50, 5018, 1985

    Cited by (2)

  • <no title>

    TOSHIMITSU A.

    Synlett 1996, 465

    Cited by (1)

  • <no title>

    RAMACHANDRAN P. V.

    Tetrahedron: Asymmetry 5, 1075, 1994

    Cited by (3)

  • <no title>

    FUJISAWA T.

    Tetrahedron: Asymmetry 5, 1095, 1994

    Cited by (4)

  • <no title>

    COREY E. J.

    Tetrahedron Lett. 32, 6835, 1991

    Cited by (2)

  • <no title>

    MIKAMI K.

    Nature 385, 613, 1997

    Cited by (5)

  • <no title>

    MATSUKAWA S.

    Tetrahedron Asymmetry 8, 815, 1997

    Cited by (3)

  • <no title>

    MATSUKAWA S.

    Enantiomer 1, 69, 1996

    Cited by (2)

  • <no title>

    idem

    Tetrahedron: Asymmetry 6, 2571, 1995

    Cited by (1)

  • <no title>

    KOBAYASHI S.

    J. Am. Chem. Soc. 116, 9805, 1994

    Cited by (7)

  • <no title>

    MUKAIYAMA T.

    Bull.Chem.Soc.Jpn. 67, 1708, 1994

    Cited by (4)

  • <no title>

    ITO Y.

    J. Am. Chem. Soc. 108, 6405, 1986

    Cited by (5)

  • <no title>

    ITO Y.

    Tetrahedron 44, 5253, 1988

    Cited by (3)

  • <no title>

    HOLLIS T. K.

    J. Am. Chem. Soc. 117, 4570, 1995

    Cited by (5)

  • <no title>

    CARREIRA E. M.

    Tetrahedron Lett. 35, 4323, 1994

    Cited by (2)

  • <no title>

    DENMARK S. E.

    Tetrahedron Lett. 35, 4327, 1994

    Cited by (2)

  • <no title>

    DENMARK S. E.

    J. Am. Chem. Soc. 113, 2177, 1991

    Cited by (2)

  • <no title>

    MIKAMI K.

    J. Am. Chem. Soc. 115, 7039, 1993

    Cited by (8)

  • <no title>

    IDEM.

    J. Am. Chem. Soc. 116, 4077, 1994

    Cited by (1)

  • <no title>

    BERNARDI A.

    J. Org. Chem. 55, 3576, 1990

    Cited by (3)

  • <no title>

    LI Y.

    J. Org. Chem. 55, 481, 1990

    Cited by (3)

  • <no title>

    SCHWESINGER R.

    Houben-Weyl E21 8, 1996

    Cited by (1)

  • <no title>

    SHARPLESS K. B.

    Aldrichim. Acta 12, 63, 1979

    Cited by (3)

  • <no title>

    HOFFMANN R. W.

    Chem. Rev. 89, 1841, 1989

    Cited by (11)

  • <no title>

    MIKAMI K.

    the 70th Annual Meeting of the Chemical Society of Japan, 1996, Abstr.

    Cited by (1)

  • <no title>

    SHINOHARA N.

    Rev. Heteroatom Chem. 14, 165, 1996

    Cited by (1)

  • <no title>

    KATAGIRI T.

    Tetrahedron: Asymmetry 10, 2583, 1999

    Cited by (2)

  • <no title>

    ISHII A.

    Tetrahedron Lett. 39, 1199, 1998

    Cited by (3)

  • <no title>

    IDEM.

    Chem. Lett. 1998, 119

    Cited by (1)

  • <no title>

    ISHII A.

    Synlett 1997, 1381

    Cited by (2)

  • <no title>

    FUNABIKI K.

    Chem. Commun. 1998, 2051

    Cited by (3)

  • <no title>

    LOH T. -P.

    Chem. Commun. 1996, 1929

    Cited by (4)

  • <no title>

    KUBOTA T.

    Tetrahedron Lett. 33, 1351, 1992

    Cited by (3)

  • <no title>

    ISEKI K.

    Tetrahedron 54, 13887, 1998

    DOI  Cited by (3)

  • <no title>

    COREY E. J.

    Tetrahedron Lett. 37, 6513, 1997

    DOI  Cited by (1)

  • <no title>

    OHKUMA T.

    J. Am. Chem. Soc. 120, 13529, 1998

    DOI  Cited by (5)

  • <no title>

    RUMMENS F. H. A.

    Org. Magn. Res. 2, 351, 1970

    DOI  Cited by (1)

  • <no title>

    SAKUMO K.

    J. Fluorine Chem. 93, 165, 1999

    DOI  Cited by (5)

Codes

  • NII Article ID (NAID)
    10008819868
  • NII NACSIS-CAT ID (NCID)
    AN0024521X
  • Text Lang
    JPN
  • Article Type
    REV
  • ISSN
    00379980
  • NDL Article ID
    5342132
  • NDL Source Classification
    ZP11(科学技術--化学・化学工業--有機化学・有機化学工業)
  • NDL Call No.
    Z17-256
  • Data Source
    CJP  NDL  J-STAGE 
Page Top