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Ugi Reaction: Chemists' Guide

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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Navnath Hatvate
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806 views11 pages

Ugi Reaction: Chemists' Guide

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

Uploaded by

Navnath Hatvate
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
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Download as PPTX, PDF, TXT or read online on Scribd
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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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