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

J Org Chem

Dipartimento di Scienze Farmaceutiche-Sezione di Chimica Generale e Organica "A. Marchesini" , Università degli Studi di Milano, Via Venezian 21 , 20133 Milano , Italy.

Published: May 2019

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 synthesize 2-spiroindolin-3-ones from 4 H-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-3 H-indolin-3-ones in moderate to good yields.

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http://dx.doi.org/10.1021/acs.joc.9b00143DOI Listing

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