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    Ugi Reaction

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    Navnath Hatvate
    The Ugi reaction is a multi-component reaction that combines a ketone or aldehyde, an amine, an isocyanide, and a carboxylic acid to form a bis-amide. It was first reported in 1959 by Prof. Ivar Karl Ugi. While the scope of the Ugi reaction has expanded in recent decades due to more available isocyanides, developing stereocontrol has been challenging without a full understanding of the reaction mechanism. The reaction proceeds through the formation of an imine intermediate followed by successive additions of the isocyanide and carboxylate components to ultimately form the bis-amide product. Lewis acid catalysts and chiral auxiliaries have been used in attempts to control reaction enant

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    Ugi Reaction

    Uploaded by

    Navnath Hatvate
    282 views11 pages
    The Ugi reaction is a multi-component reaction that combines a ketone or aldehyde, an amine, an isocyanide, and a carboxylic acid to form a bis-amide. It was first reported in 1959 by Prof. Ivar Karl Ugi. While the scope of the Ugi reaction has expanded in recent decades due to more available isocyanides, developing stereocontrol has been challenging without a full understanding of the reaction mechanism. The reaction proceeds through the formation of an imine intermediate followed by successive additions of the isocyanide and carboxylate components to ultimately form the bis-amide product. Lewis acid catalysts and chiral auxiliaries have been used in attempts to control reaction enant

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    The Ugi reaction is a multi-component reaction that combines a ketone or aldehyde, an amine, an isocyanide, and a carboxylic acid to form a bis-amide. It was first reported in 1959 by Prof. Ivar Karl Ugi. While the scope of the Ugi reaction has expanded in recent decades due to more available isocyanides, developing stereocontrol has been challenging without a full understanding of the reaction mechanism. The reaction proceeds through the formation of an imine intermediate followed by successive additions of the isocyanide and carboxylate components to ultimately form the bis-amide product. Lewis acid catalysts and chiral auxiliaries have been used in attempts to control reaction enant

    Copyright:

    © All Rights Reserved
    Download as PPTX, PDF, TXT or read online from Scribd
    Download as pptx, pdf, or txt
    282 views11 pages

    Ugi Reaction

    Uploaded by

    Navnath Hatvate
    The Ugi reaction is a multi-component reaction that combines a ketone or aldehyde, an amine, an isocyanide, and a carboxylic acid to form a bis-amide. It was first reported in 1959 by Prof. Ivar Karl Ugi. While the scope of the Ugi reaction has expanded in recent decades due to more available isocyanides, developing stereocontrol has been challenging without a full understanding of the reaction mechanism. The reaction proceeds through the formation of an imine intermediate followed by successive additions of the isocyanide and carboxylate components to ultimately form the bis-amide product. Lewis acid catalysts and chiral auxiliaries have been used in attempts to control reaction enant

    Copyright:

    © All Rights Reserved
    Download as PPTX, PDF, TXT or read online from Scribd
    Download as pptx, pdf, or txt
    of 11

    Ugi Reaction

    Dr. Navnath Hatvate


    Ugi Reaction
     Ugi reaction is a multi component reaction (MCR) between a ketone or
    aldehyde, an amine, an isocyanide and a carboxylic acid to form a bis-
    amide (α-aminoacyl amide derivatives)

     Reported first by Prof. Ivar Karl Ugi in the year 1959

     Along with the Passerini reaction, it is classified as an isocyanide-based


    multicomponent reaction
    Ugi Reaction

    Ketone
    Carboxylic Amine Isocyanide
    or Aldehyde
    acid

    -H2O

    Bis-amide
    Ugi Reaction
     Major advances in the scope of the Ugi reaction have occurred only within
    the last 20 years, mainly because of the limited availability of isocyanides
    and poor stereocontrol.
     In the mid 1900’s, only a few isocyanides were available.
     Today, about 380 isocyanides are commercially available.
     Development of stereocontrol has been difficult due to incomplete
    knowledge of the reaction mechanism.
    Ugi Reaction
     The Ugi reaction is exothermic and usually complete within minutes of
    adding the isocyanide.
     High concentration (0.5M - 2.0M) of reactants give the highest yields.
     The reaction is usually conducted in a polar protic solvent such as
    methanol, and some success in water has recently been shown
     Usually, non-polar halogenated solvents prove detrimental, as most amines
    are insoluble
    Ugi Reaction
     Mechanism
    Step 1 (Formation of Imine)
    The first step involves condensation of aldehyde 1 and amine 2 to convert into
    respective imine
    Ugi Reaction
     Step 2 (protonation of Imine)
    The Second step imine is protonated with carboxylic acid and that lead to generation of
    carboxylate ions and electron deficient center on imine carbon
    Ugi Reaction
     Step 3 (Addition of isocyanide)
    The third step addition of isocyanide is takes place on electron deficient center on
    imine’s carbon
    Ugi Reaction
     Step 4 (Attach of carboxylate)
    The fourth step attach of carboxylate is takes place on electron deficient center on
    isocyanides carbon
    Ugi Reaction
     Step 5 (Rearrangement)
    In last step nitrogen of isocyanide abstract proton from amine and generates a
    nucleophilic amine and later nucleophilic amine attach on carbon of carboxylic acid and
    then the C-O bond between the carbon of isocyanide and carboxylic acid carbon is
    breaks and that lead formation of diamides
    Lewis Acid Catalysts and Chiral Auxiliaries
     Techniques used in attempts to control enantioselectivity in the Ugi reaction have
    included Lewis acid catalysts and chiral auxiliaries

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