Challenging 50 years of established views on Ugi reaction: A theoretical approach

Nicolas Chéron; Romain Ramozzi; Laurent El Kaïm; Laurence Grimaud; Paul Fleurat-Lessard

doi:10.1021/jo2021554

Challenging 50 years of established views on Ugi reaction: A theoretical approach

Nicolas Chéron
, Romain Ramozzi
, Laurent El Kaïm
, Laurence Grimaud
, Paul Fleurat-Lessard

Research output: Contribution to journal › Article › peer-review

Abstract

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.

Original language	English
Pages (from-to)	1361-1366
Number of pages	6
Journal	Journal of Organic Chemistry
Volume	77
Issue number	3
DOIs	https://doi.org/10.1021/jo2021554
Publication status	Published - 3 Feb 2012
Externally published	Yes

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10.1021/jo2021554

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abstract = "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.",

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AU - Chéron, Nicolas

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AU - Kaïm, Laurent El

AU - Grimaud, Laurence

AU - Fleurat-Lessard, Paul

PY - 2012/2/3

Y1 - 2012/2/3

N2 - 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.

AB - 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.

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Challenging 50 years of established views on Ugi reaction: A theoretical approach

Abstract

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