Highly Enantioselective Asymmetric 1,3-Dipolar Cycloaddition of Azomethine Ylide Catalyzed by a Copper(I)/ClickFerrophos Complex

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Abstract

A copper(I)/ClickFerrophos complex catalyzed the asymmetric 1,3-dipolar cycloaddition reaction of methyl N-benzylideneglycinate (the source of azomethine ylides) with vinyl sulfone to give the exo-2,4,5-trisubstituted pyrrolidine in good yield with high enantioselectivity (99% ee). The complex also effectively catalyzed reactions of other dipolarophiles such as acrylates, maleate, and maleimides to give the exo-2,4,5-, and 2,3,4,5-substituted pyrrolidine derivatives with high diastereo- and enantioselectivities.

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This article has been cited by 12 ACS Journal articles (5 most recent appear below).

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  Ag/ThioClickFerrophos-Catalyzed Enantioselective Mannich Reaction and Amination of Glycine Schiff Base

  Kazumi Imae, Kenta Shimizu, Kenichi Ogata, and Shin-ichi Fukuzawa
  The Journal of Organic Chemistry2011 76 (9), 3604-3608

  • Ag/ThioClickFerrophos-Catalyzed Enantioselective Mannich Reaction and Amination of Glycine Schiff Base

    Kazumi Imae, Kenta Shimizu, Kenichi Ogata, and Shin-ichi Fukuzawa
    The Journal of Organic Chemistry2011 76 (9), 3604-3608

    The AgOAc/ThioClickFerrophos complex catalyzed the asymmetric Mannich reaction of glycine Schiff base with N-tosylimines effectively to give a mixture of syn and anti adducts (syn/anti = 60/40−70/30) at high yields with high enantioselectivities (up to 98%...

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• 

  N-(2-Pyridylmethyl)imines as Azomethine Precursors in Catalytic Asymmetric [3 + 2] Cycloadditions

  Silvia Padilla, Rubén Tejero, Javier Adrio, and Juan C. Carretero
  Organic Letters2010 12 (24), 5608-5611

  • N-(2-Pyridylmethyl)imines as Azomethine Precursors in Catalytic Asymmetric [3 + 2] Cycloadditions

    Silvia Padilla, Rubén Tejero, Javier Adrio, and Juan C. Carretero
    Organic Letters2010 12 (24), 5608-5611

    An efficient Cu(I)-catalyzed asymmetric [3 + 2] cycloaddition of N-(2-pyridylmethyl) imines has been developed. In the presence of a Cu(CH3CN)4PF6/bisoxazoline catalyst system, high levels of enantioselectivity (up to 97% ee) and moderate to high exo ...

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• 

  Diastereoselective Silver-Catalyzed 1,3-Dipolar Cycloaddition of Azomethine Ylides with Fluorinated Imine

  Haibo Xie, Jiangtao Zhu, Zixian Chen, Shan Li, and Yongming Wu
  The Journal of Organic Chemistry2010 75 (21), 7468-7471

  • Diastereoselective Silver-Catalyzed 1,3-Dipolar Cycloaddition of Azomethine Ylides with Fluorinated Imine

    Haibo Xie, Jiangtao Zhu, Zixian Chen, Shan Li, and Yongming Wu
    The Journal of Organic Chemistry2010 75 (21), 7468-7471

    We described hereby an instance of diastereoselective silver-catalyzed 1,3-dipolar cycloaddition of azomethine ylides with imine compounds. This new method provided synthetically useful, highly substituted tetrahydroimidazole derivatives with efficiency ...

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

  Chiral Bis(imidazolidine)pyridine−Cu(OTf)₂: Catalytic Asymmetric Endo-Selective [3 + 2] Cycloaddition of Imino Esters with Nitroalkenes

  Takayoshi Arai, Asami Mishiro, Naota Yokoyama, Kuniko Suzuki and Hiroyasu Sato
  Journal of the American Chemical Society2010 132 (15), 5338-5339

  • Chiral Bis(imidazolidine)pyridine−Cu(OTf)₂: Catalytic Asymmetric Endo-Selective [3 + 2] Cycloaddition of Imino Esters with Nitroalkenes

    Takayoshi Arai, Asami Mishiro, Naota Yokoyama, Kuniko Suzuki and Hiroyasu Sato
    Journal of the American Chemical Society2010 132 (15), 5338-5339

    The novel C2-symmetric bis(imidazolidine)pyridine (PyBidine) ligand was easily synthesized in a single condensation of 2,6-pyridyl aldehyde and optically active (S,S)-diphenylethylenediamine. In the C2-symmetric PyBidine−Cu(OTf)2 complex, imidazolidine ...

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

  Highly Endo-Selective and Enantioselective 1,3-Dipolar Cycloaddition of Azomethine Ylide with α-Enones Catalyzed by a Silver(I)/ThioClickFerrophos Complex

  Ichiro Oura, Kenta Shimizu, Kenichi Ogata and Shin-ichi Fukuzawa
  Organic Letters2010 12 (8), 1752-1755

  • Highly Endo-Selective and Enantioselective 1,3-Dipolar Cycloaddition of Azomethine Ylide with α-Enones Catalyzed by a Silver(I)/ThioClickFerrophos Complex

    Ichiro Oura, Kenta Shimizu, Kenichi Ogata and Shin-ichi Fukuzawa
    Organic Letters2010 12 (8), 1752-1755

    A silver(I)/ThioClickFerrophos complex catalyzed the highly endo-selective asymmetric 1,3-dipolar cycloaddition reaction of methyl N-benzylideneglycinate (the source of azomethine ylides) with (E)-acyclic α-enones having an endo/exo ratio of 90/10 to 99/...

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

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