Acid-Free, Aminoborane-Mediated Ugi-Type Reaction Leading to General Utilization of Secondary Amines

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Abstract

A variety of secondary amines have become utilized in the Ugi reaction by using aminoborane 1 as an iminium ion generator. Aldehydes, secondary amines, and isocyanides are coupled in the presence of 1 at room temperature, giving the corresponding α-amino amides in good yields. The nonacidic reaction conditions are beneficial for unique chemoselectivity, where the aldimine functionality is left intact in the present Ugi-type reaction.

Citing Articles

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This article has been cited by 3 ACS Journal articles (3 most recent appear below).

• 

  Copper-Catalyzed Synthesis of α-Amino Imides from Tertiary Amines: Ugi-Type Three-Component Assemblies Involving Direct Functionalization of sp³ C−Hs Adjacent to Nitrogen Atoms

  Xin Ye, Chunsong Xie, Yuanyuan Pan, Laihong Han, and Tian Xie
  Organic Letters2010 12 (19), 4240-4243

  • Copper-Catalyzed Synthesis of α-Amino Imides from Tertiary Amines: Ugi-Type Three-Component Assemblies Involving Direct Functionalization of sp³ C−Hs Adjacent to Nitrogen Atoms

    Xin Ye, Chunsong Xie, Yuanyuan Pan, Laihong Han, and Tian Xie
    Organic Letters2010 12 (19), 4240-4243

    α-Amino imides can be accessed straightforwardly from tertiary amines through copper-catalyzed three-component reactions involving the direct functionalization of sp3 C−Hs adjacent to nitrogen atoms. This reaction has demonstrated a tolerance to a wide ...

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

  Direct Preparation of Unsymmetrical Difunctionalized Cyclen Derivatives by an Ugi Multicomponent Reaction

  Giovanni Piersanti, Francesco Remi, Vieri Fusi, Mauro Formica, Luca Giorgi and Giovanni Zappia
  Organic Letters2009 11 (2), 417-420

  • Direct Preparation of Unsymmetrical Difunctionalized Cyclen Derivatives by an Ugi Multicomponent Reaction

    Giovanni Piersanti, Francesco Remi, Vieri Fusi, Mauro Formica, Luca Giorgi and Giovanni Zappia
    Organic Letters2009 11 (2), 417-420

    A new and efficient synthetic protocol for the preparation of unsymmetrical difunctionalized cyclen and its close derivatives using a modified Ugi reaction (N-split Ugi) is described. The scope of this methodology is further extended by the successful ...

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

  Comprehensive Survey of Chemical Libraries for Drug Discovery and Chemical Biology: 2007

  Roland E. Dolle, Bertrand Le Bourdonnec, Allan J. Goodman, Guillermo A. Morales, Craig J. Thomas and Wei Zhang
  Journal of Combinatorial Chemistry2008 10 (6), 753-802

  • Comprehensive Survey of Chemical Libraries for Drug Discovery and Chemical Biology: 2007

    Roland E. Dolle, Bertrand Le Bourdonnec, Allan J. Goodman, Guillermo A. Morales, Craig J. Thomas and Wei Zhang
    Journal of Combinatorial Chemistry2008 10 (6), 753-802
    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links

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