A Cu(I)-Catalyzed C−H α-Amination of Esters. Direct Synthesis of Hydantoins

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Abstract

This paper describes a novel intermolecular α-amination process of esters using CuCl as catalyst and di-tert-butyldiaziridinone as nitrogen source. A variety of hydantoins can be formed effectively under mild reaction conditions.

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

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  Gold(I)-Catalyzed Formation of 3-Pyrazolines through Cycloaddition of Diaziridine to Alkynes

  David A. Capretto, Chad Brouwer, Catherine B. Poor, and Chuan He
  Organic Letters2011 13 (21), 5842-5845

  • Gold(I)-Catalyzed Formation of 3-Pyrazolines through Cycloaddition of Diaziridine to Alkynes

    David A. Capretto, Chad Brouwer, Catherine B. Poor, and Chuan He
    Organic Letters2011 13 (21), 5842-5845

    This work reports the high-yield formation of pyrazoline derivatives mediated by gold(I) catalysts. The reaction utilizes a diaziridine, which has seen only limited usage in organic methodology. Mechanistic studies suggest a gold-mediated opening of the ...

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• 

  New Reactivity of Oxaziridine: Pd(II)-Catalyzed Aromatic C–H Ethoxycarbonylation via C–C Bond Cleavage

  Xingao Peng, Yingguang Zhu, Thomas A. Ramirez, Baoguo Zhao, and Yian Shi
  Organic Letters2011 13 (19), 5244-5247

  • New Reactivity of Oxaziridine: Pd(II)-Catalyzed Aromatic C–H Ethoxycarbonylation via C–C Bond Cleavage

    Xingao Peng, Yingguang Zhu, Thomas A. Ramirez, Baoguo Zhao, and Yian Shi
    Organic Letters2011 13 (19), 5244-5247

    A novel Pd(II)-catalyzed aromatic C–H ethoxycarbonylation with oxaziridine involving C–C bond cleavage is described. Various aromatic 2-phenylpyridines and related compounds as well as aryl ureas can be effectively ethoxycarbonylated. A catalytic cycle ...

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

  Nickel-Catalyzed Synthesis of 1,3,5-Trisubstituted Hydantoins from Acrylates and Isocyanates

  Tomoya Miura, Yusuke Mikano, and Masahiro Murakami
  Organic Letters2011 Article ASAP

  • Nickel-Catalyzed Synthesis of 1,3,5-Trisubstituted Hydantoins from Acrylates and Isocyanates

    Tomoya Miura, Yusuke Mikano, and Masahiro Murakami
    Organic Letters2011 Article ASAP

    One molecule of acrylate reacts with two molecules of isocyanate in the presence of a nickel(0)/SIPr catalyst to give a 1,3,5-trisubstituted hydantoin. Two processes operate in sequence, the first, regioselective formation of N-substituted fumaramate from ...

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

  A Copper(II)-Mediated Regioselective Cyclization−Acetoxylation of 6,8-Dien-1-ones for the Synthesis of Functionalized Cyclopentanes

  Yazhou Wang and Haifeng Du
  The Journal of Organic Chemistry2010 75 (10), 3503-3506

  • A Copper(II)-Mediated Regioselective Cyclization−Acetoxylation of 6,8-Dien-1-ones for the Synthesis of Functionalized Cyclopentanes

    Yazhou Wang and Haifeng Du
    The Journal of Organic Chemistry2010 75 (10), 3503-3506

    This paper describes a copper(II) acetate-mediated cyclization−acetoxylation of 6,8-dien-1-ones in the presence of sodium acetate as base. A variety of functionalized cyclopentanes containing synthetic useful allylic alcohol moieties with three contiguous ...

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• 

  Copper-Catalyzed Amination of Primary Benzylic C−H Bonds with Primary and Secondary Sulfonamides

  David A. Powell and Hope Fan
  The Journal of Organic Chemistry2010 75 (8), 2726-2729

  • Copper-Catalyzed Amination of Primary Benzylic C−H Bonds with Primary and Secondary Sulfonamides

    David A. Powell and Hope Fan
    The Journal of Organic Chemistry2010 75 (8), 2726-2729

    A room-temperature, copper-catalyzed amination of primary benzylic C−H bonds with primary and secondary sulfonamides is described. The reaction is applicable to the coupling of a range of primary and secondary benzylic hydrocarbons with a diverse set of ...

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

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