Challenging 50 Years of Established Views on Ugi Reaction: A Theoretical Approach

The Ugi reaction is one of the most famous multicomponent couplings, and its efficiency is still explained by the original mechanism suggested by Ugi in the 60s. This article aims to present a thorough theoretical study of this reaction. It describes how the imine is activated and how the new stereo...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 77; no. 3; pp. 1361 - 1366
Main Authors Chéron, Nicolas, Ramozzi, Romain, Kaïm, Laurent El, Grimaud, Laurence, Fleurat-Lessard, Paul
Format Journal Article
LanguageEnglish
Published Washington, DC American Chemical Society 03.02.2012
Subjects
Chemical Sciences
Chemistry
Exact sciences and technology
Kinetics and mechanisms
or physical chemistry
Organic chemistry
Reactivity and mechanisms
Theoretical and
Theoretical study
Reaction mechanism
Reversible reaction
Multicomponent reaction
Imine
Ugi reaction
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Summary:The Ugi reaction is one of the most famous multicomponent couplings, and its efficiency is still explained by the original mechanism suggested by Ugi in the 60s. This article aims to present a thorough theoretical study of this reaction. It describes how the imine is activated and how the new stereogenic center is formed. Our calculations strongly suggest alternatives to some commonly accepted features, such as the reversibility of the intermediate steps, and temper the nature of the driving force of the reaction.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:0022-3263
1520-6904
DOI:10.1021/jo2021554