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.

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]

Cycloaddition versus Alkylation Reactions of 2-Vinylindoles with α,β-Unsaturated Carbonyl Compounds Under Gold Catalysis

V. Pirovano
Primo
;
M. Dell'Acqua
Secondo
;
D. Facoetti;D. Nava;S. Rizzato;G. Abbiati
Penultimo
;
E. Rossi
Ultimo
2013

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.
Cycloaddition; Diastereoselectivity; Gold; Michael addition; Nitrogen heterocycles
Settore CHIM/06 - Chimica Organica
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/226016
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