Development of Catalytic Asymmetric Reactions Focussing on Fluoroorganic Compounds

この論文にアクセスする

この論文をさがす

著者

抄録

Highly enantioselective catalyses for preparing α, α-difluoro-β-hydroxycarboxylates and secondary α-trifluoromethyl alcohols have been developed. Difluoroketene ethyl trimethylsilyl acetal reacts with aldehydes in the presence of chiral boron complexes to afford the aldol adducts with up to 98% ee. The hydrogenation of 1, 1, 1-trifluoroalkan-2-one enol acetates using chiral ruthenium catalysts provides the secondary α-trifluoromethyl alcohols of excellent enantiopurity. The trifluoromethylation of carbonyl compounds with TMSCF<SUB>3</SUB>catalyzed by chiral quaternary ammonium fluorides or triaminosulfonium salts was assessed for synthesizing optically active α-trifluoromethyl alcohols including the tertiary alcohols which, unfortunately, gave moderate enantioselection. Throughout the course of our search for asymmetric catalysts for the trifluoromethylation, two types of Lewis bases, chiral phosphoramides and formamides, have been newly synthesized, and their successful application to the allylation of aldehydes with allylic trichlorosilanes is also described, which provide the corresponding homoallylic alcohols with good-to-excellent enantioselectivity.

収録刊行物

  • 有機合成化学協会誌

    有機合成化学協会誌 58(11), 1037-1047, 2000-11-01

    The Society of Synthetic Organic Chemistry, Japan

参考文献:  96件中 1-96件 を表示

  • <no title>

    Biomedical Aspects of Fluorine Chemistry, 1982

    被引用文献1件

  • <no title>

    WELCH J. T.

    Fluorine in Bioorganic Chemistry, 1991

    被引用文献26件

  • <no title>

    WELCH J. T.

    Selective Fluorination in Organic and Bioorganic Chemistry, 1991

    被引用文献4件

  • <no title>

    Organofluorine Compounds in Medicinal Chemistry and Biomedical Applications, 1993

    被引用文献1件

  • <no title>

    Biomedical Frontiers of Fluorine Chemistry, 1996

    被引用文献3件

  • <no title>

    WELCH J. T.

    Tetrahedron 43, 3123, 1987

    被引用文献30件

  • <no title>

    BONDI A.

    J. Phys. Chem. 68, 441, 1964

    被引用文献95件

  • <no title>

    KUSUMOTO T.

    Dyestuffs Chem 39, 6, 1994

    被引用文献1件

  • <no title>

    NOHIRA H.

    Dyestuffs Chem 39, 258, 1993

    被引用文献1件

  • <no title>

    MIKAMI K.

    Enantiocontrolled Synthesis of Fluoro-organic Compounds: Stereochemical Challenges and Biomedical Targets 557, 1999

    被引用文献1件

  • <no title>

    HIYAMA T.

    Asymmetric Fluoroorganic Chemistry: Synthesis, Applications. and Future Directions 226, 2000

    被引用文献1件

  • <no title>

    BRAVO P.

    Tetrahedron Asymmetry 1, 661, 1990

    被引用文献4件

  • <no title>

    RESNATI G.

    Tetrahedron 49, 9385, 1993

    被引用文献12件

  • <no title>

    HAYASHI T.

    Enantiocontrolled Synthesis of Fluoro-organic Compounds 5, 1994

    被引用文献1件

  • <no title>

    ISEKI K.

    Rev. Heteroatom Chem. 12, 211, 1995

    被引用文献2件

  • <no title>

    Enantiocontrolled Synthesis of Fluoro-organic Compounds: Stereochemical Challenges and Biomedical Targets, 1999

    被引用文献2件

  • <no title>

    Asymmetric Fluoroorganic Chemistry : Synthesis. Applications, and Future Directions, 2000

    被引用文献1件

  • <no title>

    SEEBACH D.

    Angew. Chem., Int. Ed. Engl. 29, 1320, 1990

    被引用文献4件

  • <no title>

    GELB M. H.

    Biochemistry 24, 1813, 1985

    被引用文献3件

  • <no title>

    SHAM H. L.

    J. Chem. Soc., Chem. Commun. 110, 1991

    被引用文献1件

  • <no title>

    KIRK K. L.

    Fluorine-containing Amino Acids 343, 1995

    被引用文献1件

  • <no title>

    PATEL D. V.

    J. Med. Chem. 36, 2431, 1993

    被引用文献2件

  • <no title>

    ROSENBERG S. H.

    Plattner, J. J. U. S. Patent, 1989

    被引用文献1件

  • <no title>

    Chem. Abstr. 110, 39369, 1989

    被引用文献1件

  • <no title>

    BRAUN M.

    Liebigs Ann. Chem. 1447, 1995

    被引用文献1件

  • <no title>

    ANDRE J. M.

    Synthesis 1070, 1996

    被引用文献1件

  • <no title>

    ISEKI K.

    Tetrahedron Lett. 38, 1447, 1997

    被引用文献2件

  • <no title>

    ISEKI K.

    Tetrahedron 53, 10271, 1997

    被引用文献2件

  • <no title>

    KITAGAWA O.

    Tetrahedron Lett. 29, 1803, 1988

    被引用文献2件

  • <no title>

    TAGUCHI T.

    Tetrahedron Lett. 29, 5291, 1988

    被引用文献5件

  • <no title>

    BURTON D. J.

    J. Fluorine Chem 38, 125, 1988

    被引用文献1件

  • <no title>

    KITAGAWA O.

    Chem. Lett. 1307, 1990

    被引用文献1件

  • <no title>

    PARMEE E. R.

    J. Am. Chem. Soc. 113, 9365, 1991

    被引用文献7件

  • <no title>

    PARMEE E. R.

    Tetrahedron. Lett. 33, 1729, 1992

    被引用文献5件

  • <no title>

    KIYOOKA S.

    J. Org. Chem. 56, 2276, 1991

    被引用文献5件

  • <no title>

    KIYOOKA S.

    Tetrahedron Lett. 33, 4927, 1992

    被引用文献6件

  • <no title>

    ISEKI K.

    Tetrahedron Lett. 38, 7209, 1997

    被引用文献1件

  • <no title>

    ISEKI K.

    Synlett 437, 1998

    被引用文献1件

  • <no title>

    ISEKI K.

    Tetrahedron 55, 2225, 1999

    被引用文献1件

  • <no title>

    ISEKI K.

    J. Fluorine Chem. 97, 85, 1999

    被引用文献1件

  • <no title>

    NAHM S.

    Tetrahedron Lett. 22, 3815, 1981

    被引用文献9件

  • <no title>

    ISEKI K.

    Tetrahedron Lett. 35, 3137, 1994

    被引用文献7件

  • <no title>

    RUPPERT I.

    Tetrahedron Lett. 25, 2195, 1984

    被引用文献3件

  • <no title>

    PRAKASH G. K. S.

    J. Am. Chem. Soc. 111, 393, 1989

    被引用文献7件

  • <no title>

    KRISHNAMURTI R.

    J. Org. Chem. 56, 984, 1991

    被引用文献7件

  • <no title>

    PRAKASH G. K. S.

    Chem. Rev. 97, 757, 1997

    被引用文献6件

  • <no title>

    ANDO A.

    Tetrahedron Lett. 34, 1507, 1993

    被引用文献2件

  • <no title>

    KUROKI Y.

    Tetrahedron Lett. 40, 8231, 1999

    被引用文献2件

  • <no title>

    MIDDLETON W. J.

    U. S. Patent, 1976

    被引用文献1件

  • <no title>

    Chem. Abstr. 85, 6388, 1976

    被引用文献1件

  • <no title>

    MIDDLETON W.

    J. Org. Synth. 64, 221, 1985

    被引用文献1件

  • <no title>

    NOYORI R.

    J. Am. Chem. Soc. 103, 2106, 1981

    被引用文献9件

  • <no title>

    RAJANBABU T. V.

    J. Org. Chem. 49, 2083, 1984

    被引用文献4件

  • <no title>

    FUJITA M.

    J. Am. Chem. Soc. 107, 8294, 1985

    被引用文献3件

  • <no title>

    HATANAKA Y.

    J. Am. Chem. Soc. 113, 7075, 1991

    被引用文献5件

  • <no title>

    ISEKI K.

    Tetrahedron Lett. 37, 5149, 1996

    被引用文献2件

  • <no title>

    ISEKI K.

    Tetrahedron 53, 3513, 1997

    被引用文献4件

  • <no title>

    FURUTA K.

    Synlett 561, 1991

    被引用文献1件

  • <no title>

    AOKI S.

    Tetrahedron 49, 1783, 1993

    被引用文献4件

  • <no title>

    GAUTHIER D. R. Jr.

    Angew. Chem. Int. Ed. Engl. 35, 2363, 1996

    被引用文献1件

  • <no title>

    KECK G. E.

    J. Am. Chent Soc. 115, 8467, 1993

    被引用文献1件

  • <no title>

    KECK G. E.

    J. Org. Chem. 58, 6543, 1993

    被引用文献3件

  • <no title>

    KECK G. E.

    Tetrahedron Lett. 34, 7827, 1993

    被引用文献2件

  • <no title>

    COSTA A. L.

    J. Am. Chem. Soc. 115, 7001, 1993

    被引用文献9件

  • <no title>

    MARSHALL J. A.

    Synlett 1992, 653

    被引用文献4件

  • <no title>

    BEDESCHI P.

    Tetrahedron Lett. 36, 7897, 1995

    被引用文献4件

  • <no title>

    YANAGISAWA A.

    J. Am. Chem. Soc. 118, 4723, 1996

    被引用文献12件

  • <no title>

    FALLER J. W.

    J. Am. Soc. Chem. 118, 1217, 1996

    被引用文献1件

  • <no title>

    WEIGAND S.

    Chem. Eur. J. 2, 1077, 1996

    被引用文献1件

  • <no title>

    YU C. -M.

    Tetrahedron Lett. 37, 7095, 1996

    被引用文献2件

  • <no title>

    DENMARK S. E.

    J. Org. Chem. 59, 5130, 1994

    被引用文献4件

  • <no title>

    DENMARK S. E.

    J. Org. Chem. 59, 5133, 1994

    被引用文献1件

  • <no title>

    KOBAYASHI S.

    Synthesis 457, 1994

    被引用文献1件

  • <no title>

    KOBAYASHI S.

    J. Org. Chem. 59, 6620, 1994

    被引用文献10件

  • <no title>

    DENMARK S. E.

    J. Org. Chem. 59, 6161, 1994

    被引用文献13件

  • <no title>

    KOBAYASHI S.

    Tetrahedron Lett. 36, 6729, 1995

    被引用文献3件

  • <no title>

    NAKAJIMA M.

    J. Am. Chem. Soc. 120, 6419, 1998

    被引用文献7件

  • <no title>

    PEYRONEL J. -F.

    J. Org. Chem. 52, 5320, 1987

    被引用文献1件

  • <no title>

    ISEKI K.

    Tetrahedron Lett. 39, 2767, 1998

    被引用文献4件

  • <no title>

    ISEKI K.

    Tetrahedron 55, 977, 1999

    被引用文献3件

  • <no title>

    ISEKI K.

    Tetrahedron: Asymmetry 9, 2889, 1998

    被引用文献1件

  • <no title>

    KUROKI Y.

    Tetrahedron Lett. 41, 4603, 2000

    被引用文献1件

  • <no title>

    KOENIG K. E.

    J. Org. Chem. 45, 2362, 1980

    被引用文献2件

  • <no title>

    BURK M. J.

    J. Am. Chem. Soc. 113, 8518, 1991

    被引用文献2件

  • <no title>

    COREY E. J.

    Tetrahedron Lett 31, 611, 1990

    被引用文献2件

  • <no title>

    MASHIMA K.

    J. Chem. Soc., Chem. Commun. 1208, 1989

    被引用文献1件

  • <no title>

    MASHIMA K.

    J. Org. Chem. 59, 3064, 1994

    被引用文献9件

  • <no title>

    NOYORI R.

    J. Am. Chem. Soc. 109, 5856, 1987

    被引用文献8件

  • <no title>

    CEREGHETTI M.

    The catalyst 56

    被引用文献1件

  • <no title>

    SCHONHOLZED P.

    Helv. Chim. Acta. 71, 897, 1988

    被引用文献1件

  • <no title>

    BURK M. J.

    J. Am. Chem. Soc. 115, 10125, 1993

    被引用文献6件

  • <no title>

    HOWARD J. A. K.

    Tetrahedron 52, 12613, 1996

    DOI 被引用文献4件

  • Fluoroorganic Chemistry: Synthetic Challenges and Biomedical Rewards;

    RESNATI G.

    Tetrahedron 52, 1996

    DOI 被引用文献1件

  • <no title>

    ISHIHARA K.

    J. Am. Chem. Soc. 115, 11490, 1993

    DOI 被引用文献8件

  • <no title>

    KOBAYASHI S.

    Tetrahedron Lett. 34, 3453, 1993

    DOI 被引用文献10件

  • <no title>

    OHKUMA T.

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

    DOI 被引用文献5件

各種コード

  • NII論文ID(NAID)
    10008821995
  • NII書誌ID(NCID)
    AN0024521X
  • 本文言語コード
    ENG
  • 資料種別
    REV
  • ISSN
    00379980
  • NDL 記事登録ID
    5549663
  • NDL 雑誌分類
    ZP11(科学技術--化学・化学工業--有機化学・有機化学工業)
  • NDL 請求記号
    Z17-256
  • データ提供元
    CJP書誌  NDL  J-STAGE 
ページトップへ