シトクロムP-450酵素を範とするルテニウム触媒を用いる酸化触媒反応の開拓 Development of Ruthenium Catalyzed Oxidation Reactions Inspired by Cytochrome P-450

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Simulation of the functions of cytochrome P-450 with transition-metal catalysts such as ruthenium complex catalysts led to the discovery of biomimetic catalytic oxidation reactions of various substrates such as amines, amides, olefins, alcohols, phenols, ketones and hydrocarbons. These catalytic reactions are practical and highly useful for synthesis of biologically active compounds, which include cortisone acetate and adriamicine acetate. Importantly, (1<I>R</I>, 3<I>S</I>) -3- [1'- (<I>t</I>-butyldimethylsilyloxy) ethyl] azetidi-2-one can be converted to the corresponding 4-acetoxyazetidinone, which is a versatile and key intermediate for the synthesis of carbapenem antibiotics, with extremely high diastereoselectivity (99% yield, 99% de). This becomes important industrial process. The oxidations of amines and amides provide highly useful 4 methods for introduction of a substituent at the α-position of amines by the oxidation of amines and amides and subsequent treatment with nucleophiles.

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  • 有機合成化学協会誌 : JOURNAL OF Synthetic Organic Chemistry JAPAN

    有機合成化学協会誌 : JOURNAL OF Synthetic Organic Chemistry JAPAN 65(1), 2-13, 2007-01-01

    The Society of Synthetic Organic Chemistry, Japan

参考文献:  74件中 1-74件 を表示

  • <no title>

    MURAHASHI S.-I.

    Angew. Chem., Int. Ed. Engl. 34, 2443, 1995

    被引用文献1件

  • <no title>

    MURAHASHI S.-I.

    Pure Appl. Chem. 64, 403, 1992

    被引用文献1件

  • <no title>

    MURAHASHI S.-I.

    Biomimetic Oxidations Catalyzed by Transition Metal Complexes, 2000

    被引用文献1件

  • <no title>

    MURAHASHI S.-I.

    Ruthenium in Organic Synthesis, 2004

    被引用文献1件

  • <no title>

    MURAHASHI S.-I.

    Modern Oxidation Methods, 2004

    被引用文献1件

  • <no title>

    SATO R.

    Cytochrome P-450, 1978

    被引用文献1件

  • <no title>

    MCMURRY T. J.

    Cytochrome P-450 : Structure, Mechanism and Biochemistry, 1986

    被引用文献1件

  • <no title>

    MURAHASHI S.-I.

    Tetrahedron Lett. 23, 229, 1982

    被引用文献1件

  • <no title>

    MURAHASHI S.-I.

    J. Am. Chem Soc. 108, 7846, 1986

    被引用文献1件

  • <no title>

    MURAHASHI S.-I.

    J. Org. Chem. 52, 4319, 1987

    被引用文献1件

  • <no title>

    MURAHASHI S.-I.

    J. Am. Chem. Soc. 110, 8256, 1988

    被引用文献1件

  • <no title>

    MURAHASHI S.-I.

    Tetrahedron 50, 453, 1994

    被引用文献1件

  • <no title>

    MURAHASHI S.-I.

    J. Org. Chem. 58, 1538, 1993

    被引用文献1件

  • <no title>

    MURAHASHI S.-I.

    Tetrahedron Lett. 33, 6991, 1992

    被引用文献1件

  • <no title>

    MURAHASHI S.-I.

    J. Chem. Soc., Chem. Commun., 1985

    被引用文献1件

  • <no title>

    MURAHASHI S.-I.

    J. Am. Chem. Soc. 111, 5002, 1989

    被引用文献1件

  • <no title>

    MURAHASHI S.-I.

    J. Org. Chem. 55, 1736, 1990

    被引用文献1件

  • <no title>

    MURAHASHI S.-I.

    Org. Synth. 70, 265, 1991

    被引用文献1件

  • <no title>

    MURAHASHI S.-I.

    J. Org. Chem. 59, 6170, 1994

    被引用文献1件

  • <no title>

    MURAHASHI S.-I.

    Tetrahedron Lett. 28, 2383, 1987

    被引用文献1件

  • <no title>

    MURAHASHI S.-I.

    J. Am. Chem. Soc. 112, 7820, 1990

    被引用文献1件

  • <no title>

    MURAHASHI S.-I.

    Tetrahedron Lett. 41, 10254, 2000

    被引用文献1件

  • <no title>

    MURAHASHI S.-I.

    Tetrahedron Lett. 32, 2145, 1991

    被引用文献1件

  • <no title>

    MURAHASHI S.-I.

    Tetrahedron Lett. 32, 5991, 1991

    被引用文献1件

  • <no title>

    BEAK P.

    Acc. Chem. Res. 29, 552, 1996

    被引用文献1件

  • <no title>

    MURAHASHI S.-I.

    Angew. Chem. Int. Ed. 44, 6931, 2005

    被引用文献1件

  • <no title>

    NORTH M.

    Angew. Chem. Int. Ed. 43, 4126, 2004

    被引用文献1件

  • <no title>

    MURAHASHI S.-I.

    J. Org. Chem. 58, 2929, 1993

    被引用文献1件

  • <no title>

    HOTOPP T.

    Tetrahedron Lett. 42, 3343, 2001

    被引用文献1件

  • <no title>

    MURAHASHI S.-I.

    Chem. Lett., 1993

    被引用文献1件

  • <no title>

    JOHNSON R. A.

    Catalytic Asymmetric Synthesis, 1993

    被引用文献1件

  • <no title>

    IMADA Y.

    Tetrahedron Lett. 33, 5081, 1992

    被引用文献1件

  • <no title>

    MURAHASHI S.-I.

    Synlett, 1995

    被引用文献1件

  • <no title>

    MURAHASHI S.-I.

    Tetrahedron Lett. 26, 925, 1985

    被引用文献1件

  • <no title>

    MURAHASHI S.-I.

    Adv. Met. Org. Chem. 3, 225, 1994

    被引用文献1件

  • <no title>

    MURAHASHI S.-I.

    Synthesis, 1993

    被引用文献1件

  • <no title>

    MURAHASHI S.-I.

    Synlett, 1989

    被引用文献1件

  • <no title>

    MURAHASHI S.-I.

    J. Org. Chem. 51, 898, 1986

    被引用文献1件

  • <no title>

    MURAHASHI S.-I.

    J. Org. Chem. 58, 7318, 1993

    被引用文献1件

  • <no title>

    MURAHASHI S.-I.

    J. Am. Chem. Soc. 118, 2509, 1996

    被引用文献1件

  • <no title>

    MURAHASHI S.-I.

    Tetrahedron Lett. 33, 7557, 1992

    被引用文献1件

  • <no title>

    MURAHASHI S.-I.

    Tetrahedron Lett. 34, 1299, 1993

    被引用文献1件

  • <no title>

    MURAHASHI S.-I.

    J. Org. Chem. 65, 9186, 2000

    被引用文献1件

  • <no title>

    MURAHASHI S.-I.

    Tetrahedron Lett. 35, 7953, 1994

    被引用文献1件

  • <no title>

    KOMIYA N.

    Chem. Commun., 2001

    被引用文献1件

  • <no title>

    MURAHASHI S.-I.

    J. Am. Chem. Soc. 114, 7913, 1992

    被引用文献1件

  • <no title>

    MURAHASHI S.-I.

    J. Chem. Soc., Chem. Commun., 1993

    被引用文献1件

  • <no title>

    MURAHASHI S.-I.

    Tetrahedron Lett. 36, 8059, 1995

    被引用文献1件

  • <no title>

    MURAHASHI S.-I.

    Synlett, 2003

    被引用文献1件

  • <no title>

    MURAHASHI S.-I.

    Pure & Appl. Chem. 73, 311, 2001

    被引用文献1件

  • <no title>

    MURAHASHI S.-I.

    Adv. Synth. Catal. 346, 195, 2004

    被引用文献1件

  • <no title>

    MURAHASHI S.-I.

    Tetrahedron : Asymmetry 16, 3527, 2005

    被引用文献1件

  • <no title>

    IMADA Y.

    Angew. Chem. Int. Ed. 44, 1704, 2005

    被引用文献1件

  • <no title>

    MURAHASHI S.-I.

    Acc. Chem. Res. 33, 225, 2000

    被引用文献1件

  • <no title>

    村橋俊一

    有合化 61, 425, 2003

    被引用文献1件

  • <no title>

    MURAHASHI S.-I.

    Catalysis Today 41, 339, 1998

    DOI 被引用文献1件

  • <no title>

    NAOTA T.

    Chem. Rev. 98, 2599, 1998

    被引用文献13件

  • <no title>

    GROVES J. T.

    J. Am. Chem. Soc. 101, 1032-1033, 1979

    被引用文献8件

  • <no title>

    MURAHASHI S.-I.

    J. Org. Chem. 44, 2408, 1979

    被引用文献3件

  • <no title>

    MURAHASHI S.-I.

    Tetrahedron Lett. 22, 5327, 1981

    被引用文献3件

  • <no title>

    MURAHASHI S.-I.

    J. Am. Chem. Soc. 100, 348, 1978

    被引用文献1件

  • <no title>

    MURAHASHI S.-I.

    J. Am. Chem. Soc. 101, 7429, 1979

    被引用文献1件

  • <no title>

    HEIMBROOK D. C.

    J. Am. Chem Soc. 106, 1514, 1984

    被引用文献1件

  • <no title>

    ISHITANI H.

    J. Am. Chem. Soc. 119, 7153-7154, 1997

    被引用文献8件

  • <no title>

    NAOTA T.

    Tetrahedron Lett. 31, 7475, 1990

    被引用文献3件

  • <no title>

    MURAHASHI S. I.

    J. Am. Chem. Soc. 125, 15312, 2003

    DOI 被引用文献2件

  • <no title>

    OSTOVIC D.

    J. Am. Chem. Soc. 111, 6511, 1989

    DOI 被引用文献2件

  • <no title>

    TRAYLOR T. G.

    J. Am. Chem. Soc. 109, 2770, 1987

    被引用文献1件

  • A greatly improved procedure for ruthenium tetroxide catalyzed oxidations of organic compounds

    CARLSEN P. H. J.

    J. Org. Chem. 46, 3936-3938, 1981

    DOI 被引用文献14件

  • <no title>

    GROVES J. T.

    J. Am. Chem. Soc. 118, 8961, 1996

    被引用文献1件

  • <no title>

    KOMIYA N.

    Tetrahedron Lett. 37, 1633, 1996

    被引用文献1件

  • <no title>

    KOMIYA N.

    J. Mol. Catal. A : Chem. 117, 21, 1997

    被引用文献1件

  • <no title>

    KOMIYA N.

    Tetrahedron Lett. 39, 7921, 1998

    被引用文献1件

  • <no title>

    IMADA Y.

    J. Am. Chem. Soc. 125, 2868, 2003

    被引用文献3件

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