分子内Heck反応による4級炭素の触媒的不斉構築 : 合成手法としての発展と反応機構の探究  [in Japanese] Catalytic Asymmetric Synthesis of Quaternary Carbon Centers by Intramolecular Heck Reaction : Synthetic Developments and Mechanistic Studies  [in Japanese]

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Abstract

Within the last decade, the enormous synthetic potential of the Heck reaction has been revealed. When employed intramolecularly, Heck reactions succeed in even forming quaternary carbon centers. The ability of intramolecular Heck reactions to reliably fashion carbon-carbon bonds in polyfunctional molecules has led to wide application of this reaction at the strategy level for the synthesis of complex natural products. One of the most important developments in this area is the increasing success being realized in effecting catalytic asymmetric Heck reactions using enantiopure ligands. Although only modest enantiocontrol was achieved in early stages, many asymmetric Heck reactions have now been demonstrated that proceed with >90% ee. Another development of the Heck reaction has led to greater understanding of its mechanistic details with two distinct pathways, the neutral and cationic pathways, being recognized. This review summarizes the synthetic developments of the intramolecular asymmetric Heck reaction for forming quaternary carbon centers and the mechanistic factors recently revealed to effect enantioselectiv- ity.

Journal

  • Journal of Synthetic Organic Chemistry, Japan

    Journal of Synthetic Organic Chemistry, Japan 58(8), 718-727, 2000-08-01

    The Society of Synthetic Organic Chemistry, Japan

References:  66

  • <no title>

    MIZOROKI T.

    Bull. Chem. Soc. Jpn. 44, 581, 1971

    Cited by (11)

  • <no title>

    HECK R. F.

    J. Org. Chem. 37, 2320, 1972

    Cited by (14)

  • <no title>

    HECK R. F.

    Organic Reactions 27, 345, 1972

    Cited by (1)

  • <no title>

    HECK R. F.

    Comprehensive Organic Synthesis 4, 833, 1991

    Cited by (1)

  • <no title>

    DAVIES G. D.

    Chem. Rev. 89, 1433, 1989

    Cited by (1)

  • <no title>

    DE MEIJERE A.

    Meyer, Angew. Chem., Int. Ed. Engl. 33, 2379, 1994

    Cited by (1)

  • <no title>

    GIBSON S. E.

    Contemp. Org. Synth. 3, 447, 1996

    Cited by (1)

  • <no title>

    BRASE S.

    Metal-Catalyzed Cross Coupling Reactions, 1998

    Cited by (2)

  • <no title>

    LINK J. T.

    Metal-Catalyzed Cross Coupling Reactions, 1998

    Cited by (1)

  • <no title>

    SHIBASAKI M.

    Advances in Metal-Organic Chemistry 119, 1996

    Cited by (1)

  • <no title>

    SHIBASAKI M.

    Tetrahedron 53, 7371, 1997

    Cited by (5)

  • <no title>

    SHIBASAKI M.

    J. Organoment. Chem. 576, 1, 1999

    Cited by (1)

  • <no title>

    COREY E. J.

    Angew. Chem., Int. Ed. Engl 37, 388, 1998

    Cited by (3)

  • <no title>

    SATO Y.

    J. Org. Chem. 54, 4738, 1989

    Cited by (6)

  • <no title>

    CARPENTER N. E.

    J. Org. Chem. 54, 5846, 1989

    Cited by (5)

  • <no title>

    CABRI W.

    Acc. Chem. Res. 28, 2, 1995

    Cited by (3)

  • <no title>

    CABRI W.

    J. Org. Chem. 56, 5796, 1991

    Cited by (2)

  • <no title>

    OZAWA F.

    J. Am. Chem. Soc. 113, 1417, 1991

    Cited by (6)

  • <no title>

    OZAWA F.

    Organometallics 12, 4188, 1993

    Cited by (7)

  • <no title>

    TAKEMOTO T.

    J. Am. Chem. Soc. 115, 8477, 1993

    Cited by (2)

  • <no title>

    KOJIMA A.

    J. Org. Chem. 61, 4876, 1996

    Cited by (2)

  • <no title>

    KOJIMA A.

    Synthesis 1998, 581

    Cited by (1)

  • <no title>

    SHIBASAKI M.

    J. Heterocyclic Chem. 35, 1057, 1998

    Cited by (1)

  • <no title>

    KONDO K.

    J. Org. Chem. 60, 4322, 1995

    Cited by (1)

  • <no title>

    idem

    Asymmetry 6, 2453, 1995

    Cited by (1)

  • <no title>

    NAKANISHI K.

    Natural Products Chemistry 1, 3, 1983

    Cited by (1)

  • <no title>

    KUEHNE M. E.

    J. Org. Chem. 35, 161, 1970

    Cited by (1)

  • <no title>

    BELL R. A.

    J. Org. Chem. 27, 3741, 1962

    Cited by (1)

  • <no title>

    CHIU C. K-F.

    J. Org. Chem. 59, 311, 1994

    Cited by (1)

  • <no title>

    RIPA L.

    J. Org. Chem. 62, 595, 1997

    Cited by (1)

  • <no title>

    idem

    J. Org. Chem. 61, 7147, 1996

    Cited by (1)

  • <no title>

    LOISELEUR O.

    Synthesis 1997, 1338

    Cited by (2)

  • <no title>

    LOISELEUR O.

    Angew. Chem., Int. Ed. Engl. 35, 200, 1996

    Cited by (2)

  • <no title>

    CHO S. Y.

    Tetrahedron Lett. 39, 1773, 1998

    Cited by (5)

  • <no title>

    HONZAWA S.

    Tetrahedron Lett. 40, 311, 1999

    Cited by (1)

  • <no title>

    DIAZ P.

    Tetrahedron 54, 4579, 1998

    Cited by (1)

  • <no title>

    ASHIMORI A.

    J. Org. Chem. 57, 4571, 1992

    Cited by (3)

  • <no title>

    OVERMAN L. E.

    Int. Ed. Engl. 36, 518, 1997

    Cited by (1)

  • <no title>

    MATSUURA T.

    J. Am. Chem. Soc. 120, 6500, 1998

    Cited by (1)

  • <no title>

    LANDIS C. R.

    J. Am. Chem. Soc. 109, 1746, 1987

    Cited by (3)

  • <no title>

    AMATORE C.

    J. Am. Chem. Soc. 113, 8375, 1991

    Cited by (1)

  • <no title>

    AMATORE C.

    Organometallics 14, 1818, 1995

    Cited by (2)

  • <no title>

    AMATORE C.

    J. Am. Chem. Soc. 115, 9531, 1993

    Cited by (1)

  • <no title>

    AMATORE C.

    J. Am. Chem. Soc. 119, 5176, 1997

    Cited by (1)

  • <no title>

    WOLFE J. P.

    J. Am. Chem. Soc. 118, 7215, 1996

    Cited by (5)

  • <no title>

    JUTAND A.

    Organometallics 14, 1810, 1995

    Cited by (2)

  • <no title>

    STANG P. J.

    J. Am. Chem. Soc. 111, 3347, 1989

    Cited by (1)

  • <no title>

    STANG P. J.

    J. Am. Chem. Soc. 111, 3356, 1989

    Cited by (2)

  • <no title>

    HINKLE R. J.

    J. Org. Chem. 55, 5033, 1990

    Cited by (2)

  • <no title>

    BROWN J. M.

    Angew. Chem., Int. Ed. Engl. 35, 657, 1996

    Cited by (2)

  • <no title>

    BROWN J. M.

    Organometallics 14, 207, 1995

    Cited by (1)

  • <no title>

    CROSS R. J.

    Adv. Inorg. Chem. 34, 219, 1989

    Cited by (1)

  • <no title>

    TOBE M. L.

    Comprehensive Coordination Chemistry 1, 281, 1987

    Cited by (1)

  • <no title>

    ROMERO R.

    Comments Inorg. Chem. 11, 21, 1990

    Cited by (1)

  • <no title>

    ALBANO V. G.

    Organometallics 9, 1269, 1990

    Cited by (1)

  • <no title>

    ALBANO V. G.

    Coord. Chem. Rev. 133, 67, 1994

    Cited by (1)

  • <no title>

    PORTNOY M.

    Organometallics 13, 3465, 1994

    Cited by (2)

  • <no title>

    KOJIMA A.

    Tetrahedron Lett. 38, 3459, 1997

    Cited by (1)

  • <no title>

    今本恒雄

    有合化 56, 511, 1998

    Cited by (1)

  • <no title>

    LAU S. Y. W

    Synlett 1999, 605

    Cited by (1)

  • <no title>

    MADDAFORD S. P.

    J. Am. Chem. Soc. 118, 10766, 1996

    DOI  Cited by (1)

  • <no title>

    ASHIMORI A.

    J. Am. Chem. Soc. 120, 6477, 1998

    DOI  Cited by (1)

  • <no title>

    ASHIMORI A.

    J. Am. Chem. Soc. 120, 6488, 1998

    DOI  Cited by (2)

  • <no title>

    ASHIMORI A.

    J. Org. Chem. 58, 6949, 1993

    DOI  Cited by (2)

  • <no title>

    PUCHOT C.

    J. Am. Chem. Soc. 108, 2353, 1986

    DOI  Cited by (9)

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    UOZUMI YASUHIRO , DANJO HIROSHI

    Farumashia 35(7), 711-715, 1999

    J-STAGE  References (20) Cited by (1)

Codes

  • NII Article ID (NAID)
    10008821039
  • NII NACSIS-CAT ID (NCID)
    AN0024521X
  • Text Lang
    JPN
  • Article Type
    REV
  • ISSN
    00379980
  • NDL Article ID
    5431874
  • 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 
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