A New Series of Organocatalysts for Diels-Alder Cycloaddition Reactions and Theoretical Analysis

Author(s): Alessandro Casoni, Elena Borsini, Alessandro Contini, Alessandro Ruffoni, Sara Pellegrino, Francesca Clerici.

Journal Name: Current Organic Chemistry

Volume 15 , Issue 19 , 2011

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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

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Article Details

VOLUME: 15
ISSUE: 19
Year: 2011
Page: [3514 - 3522]
Pages: 9
DOI: 10.2174/138527211797374788
Price: $58

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