Enantioselective Synthesis of Trifluoromethyl-Substituted Cyclopropanes

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Abstract

The reaction of 1-aryl-2,2,2-trifluorodiazoethanes with alkenes, catalyzed by the adamantylglycine-derived dirhodium complex Rh₂(R-PTAD)₄, generates trifluoromethyl-substituted cyclopropanes with high diastereoselectivity (>94%) and enantioselectivity (88−>98%).

Citing Articles

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This article has been cited by 11 ACS Journal articles (5 most recent appear below).

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  β-(Trifluoromethyl)vinyl Sulfonium Salts: Preparation and Reactions with Active Methylene and Methenyl Compounds

  Hao Lin, Qilong Shen, and Long Lu
  The Journal of Organic Chemistry2011 Article ASAP

  • β-(Trifluoromethyl)vinyl Sulfonium Salts: Preparation and Reactions with Active Methylene and Methenyl Compounds

    Hao Lin, Qilong Shen, and Long Lu
    The Journal of Organic Chemistry2011 Article ASAP

    Two trifluoromethyl-substituted building blocks β-(trifluoromethyl)vinyl sulfonium salts 1 and 2 were developed. Reactions of β-(trifluoromethyl)vinyl sulfonium salt 1 with active methylene compounds containing electron-withdrawing groups using DBU as the ...

    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
• 

  Catalytic Asymmetric C–H Insertions of Rhodium(II) Azavinyl Carbenes

  Stepan Chuprakov, Jamal A. Malik, Mikhail Zibinsky, and Valery V. Fokin
  Journal of the American Chemical Society2011 133 (27), 10352-10355

  • Catalytic Asymmetric C–H Insertions of Rhodium(II) Azavinyl Carbenes

    Stepan Chuprakov, Jamal A. Malik, Mikhail Zibinsky, and Valery V. Fokin
    Journal of the American Chemical Society2011 133 (27), 10352-10355

    A highly efficient enantioselective C–H insertion of azavinyl carbenes into unactivated alkanes has been developed. These transition metal carbenes are directly generated from readily available and stable 1-sulfonyl-1,2,3-triazoles in the presence of ...

    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
• 

  Iron-Catalyzed Preparation of Trifluoromethyl Substituted Vinyl- and Alkynylcyclopropanes

  Bill Morandi, Jeremy Cheang, and Erick M. Carreira
  Organic Letters2011 13 (12), 3080-3081

  • Iron-Catalyzed Preparation of Trifluoromethyl Substituted Vinyl- and Alkynylcyclopropanes

    Bill Morandi, Jeremy Cheang, and Erick M. Carreira
    Organic Letters2011 13 (12), 3080-3081

    A convenient iron-catalyzed procedure to prepare trifluoromethylated vinyl- and alkynylcyclopropanes in a chemo- and diastereoselective manner is presented. The active diazo compound (trifluoromethyl diazomethane) is generated in situ and used in the ...

    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
• 

  Enabling the Synthesis of Perfluoroalkyl Bicyclobutanes via 1,3 γ-Silyl Elimination

  Christopher B. Kelly, Allison M. Colthart, Brad D. Constant, Sean R. Corning, Lily N. E. Dubois, Jacqueline T. Genovese, Julie L. Radziewicz, Ellen M. Sletten, Katherine R. Whitaker, and Leon J. Tilley
  Organic Letters2011 13 (7), 1646-1649

  • Enabling the Synthesis of Perfluoroalkyl Bicyclobutanes via 1,3 γ-Silyl Elimination

    Christopher B. Kelly, Allison M. Colthart, Brad D. Constant, Sean R. Corning, Lily N. E. Dubois, Jacqueline T. Genovese, Julie L. Radziewicz, Ellen M. Sletten, Katherine R. Whitaker, and Leon J. Tilley
    Organic Letters2011 13 (7), 1646-1649

    Two new bicyclobutanes were prepared from cyclobutyl systems by a novel, solvolytic, carbocation-based methodology. An electron-withdrawing perfluoroalkyl group at the incipient cationic center enhances neighboring-group participation of the γ-silyl group,...

    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
• 

  Enantioenriched Synthesis of Cyclopropenes with a Quaternary Stereocenter, Versatile Building Blocks

  Misaki Uehara, Hidehiro Suematsu, Yoichi Yasutomi, and Tsutomu Katsuki
  Journal of the American Chemical Society2011 133 (2), 170-171

  • Enantioenriched Synthesis of Cyclopropenes with a Quaternary Stereocenter, Versatile Building Blocks

    Misaki Uehara, Hidehiro Suematsu, Yoichi Yasutomi, and Tsutomu Katsuki
    Journal of the American Chemical Society2011 133 (2), 170-171

    Ir(salen) complexes were found to catalyze enantioselective cyclopropenation efficiently. Cyclopropenation can be carried out using either a donor/acceptor- or an acceptor/acceptor-substituted diazo compound such as α-aryl-α-diazoacetates, α-phenyl-α-...

    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links

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