Merging the ability of cationic gold(I) catalysts to activate unsaturated π-systems with the electrophiles driven ring-opening reactions of furans, we describe a new approach to 2-spiroindolin-3-ones from 4H-furo[3,2-b]indoles. The reaction occurs through a cascade sequence involving addition of a gold-activated allene to the furan moiety of the starting furoindole followed by a ring-opening/ring-closing event affording 2-spirocyclopentane-1,2-dihydro-3H-indolin-3-ones in moderate to good yields.

Gold-Catalyzed Cascade Reactions of 4H-Furo[3,2-b]indoles with Allenamides: Synthesis of Indolin-3-one Derivatives / V. Pirovano, E. Brambilla, S. Rizzato, G. Abbiati, M. Bozzi, E. Rossi. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - (2019 Mar). [Epub ahead of print] [10.1021/acs.joc.9b00143]

Gold-Catalyzed Cascade Reactions of 4H-Furo[3,2-b]indoles with Allenamides: Synthesis of Indolin-3-one Derivatives

V. Pirovano;E. Brambilla;S. Rizzato;G. Abbiati;E. Rossi
2019

Abstract

Merging the ability of cationic gold(I) catalysts to activate unsaturated π-systems with the electrophiles driven ring-opening reactions of furans, we describe a new approach to 2-spiroindolin-3-ones from 4H-furo[3,2-b]indoles. The reaction occurs through a cascade sequence involving addition of a gold-activated allene to the furan moiety of the starting furoindole followed by a ring-opening/ring-closing event affording 2-spirocyclopentane-1,2-dihydro-3H-indolin-3-ones in moderate to good yields.
Settore CHIM/06 - Chimica Organica
mar-2019
9-apr-2019
Article (author)
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/637458
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