Cycloaddition versus Alkylation Reactions of 2-Vinylindoles with α,β-Unsaturated Carbonyl Compounds Under Gold Catalysis
Articolo
Data di Pubblicazione:
2013
Citazione:
Cycloaddition versus Alkylation Reactions of 2-Vinylindoles with α,β-Unsaturated Carbonyl Compounds Under Gold Catalysis / V. Pirovano, M. Dell'Acqua, D. Facoetti, D. Nava, S. Rizzato, G. Abbiati, E. Rossi. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1434-193X. - 2013:28(2013 Oct), pp. 6267-6279. [10.1002/ejoc.201300725]
Abstract:
The gold-catalyzed intermolecular Diels–Alder cycloaddition and competitive Michael addition reactions between 2-vinylindoles and enones/enals are reported. The reaction outcome strictly correlates with the electronic character of the heteroaromatic substrate. Thus, Diels–Alder cycloadducts are the sole products in the presence of less electron-rich heterocycles, whereas Michael addition adducts are observed with more electron-rich heterocycles. Plausible competitive reaction mechanisms are proposed and discussed as well.
Tipologia IRIS:
01 - Articolo su periodico
Keywords:
Cycloaddition; Diastereoselectivity; Gold; Michael addition; Nitrogen heterocycles
Elenco autori:
V. Pirovano, M. Dell'Acqua, D. Facoetti, D. Nava, S. Rizzato, G. Abbiati, E. Rossi
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