Abstract
A new series of organocatalysts able to catalyse Diels-Alder cycloaddition reactions of α,β-unsaturated aldehydes was studied from both synthetic and theoretical perspectives. The importance of the imidazolidinone scaffold and the influence of the functional groups upon the formation of the reactive species was evaluated. Moreover taking into account that all these new organocatalysts gave the exo-cycloadducts as the major isomers with high selectivity a theoretical study was realized to try and define the essential features determining the observed stereochemical preference.
Keywords: Cycloadditions, computational studies, diastereoselectivity, enantioselectivity, imidazolidin-4-ones, organocatalysis, LUMO-lowering catalysts, Diels-Alder Reactions, Cinnamaldehyde, exo-cycloadducts, alpha,beta-unsaturated aldehydes, enantioselective organocatalytic transformation, MacMillan Imidazolidinone-catalysed Diels-Alder Cycloaddition, B3LYP, MPW1B95
Current Organic Chemistry
Title: A New Series of Organocatalysts for Diels-Alder Cycloaddition Reactions and Theoretical Analysis
Volume: 15 Issue: 19
Author(s): Alessandro Casoni, Elena Borsini, Alessandro Contini, Alessandro Ruffoni, Sara Pellegrino and Francesca Clerici
Affiliation:
Keywords: Cycloadditions, computational studies, diastereoselectivity, enantioselectivity, imidazolidin-4-ones, organocatalysis, LUMO-lowering catalysts, Diels-Alder Reactions, Cinnamaldehyde, exo-cycloadducts, alpha,beta-unsaturated aldehydes, enantioselective organocatalytic transformation, MacMillan Imidazolidinone-catalysed Diels-Alder Cycloaddition, B3LYP, MPW1B95
Abstract: A new series of organocatalysts able to catalyse Diels-Alder cycloaddition reactions of α,β-unsaturated aldehydes was studied from both synthetic and theoretical perspectives. The importance of the imidazolidinone scaffold and the influence of the functional groups upon the formation of the reactive species was evaluated. Moreover taking into account that all these new organocatalysts gave the exo-cycloadducts as the major isomers with high selectivity a theoretical study was realized to try and define the essential features determining the observed stereochemical preference.
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Cite this article as:
Casoni Alessandro, Borsini Elena, Contini Alessandro, Ruffoni Alessandro, Pellegrino Sara and Clerici Francesca, A New Series of Organocatalysts for Diels-Alder Cycloaddition Reactions and Theoretical Analysis, Current Organic Chemistry 2011; 15 (19) . https://dx.doi.org/10.2174/138527211797374788
DOI https://dx.doi.org/10.2174/138527211797374788 |
Print ISSN 1385-2728 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-5348 |
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