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3-Alkenyl-2-silyloxyindoles: an enabling, yet understated progeny of vinylogous carbon nucleophiles

Rassu, Gloria Maria Rita and Zambrano, Vincenzo and Tanca, Rossella and Sartori, Andrea and Battistini, Lucia and Zanardi, Franca and Curti, Claudio and Casiraghi, Giovanni (2012) 3-Alkenyl-2-silyloxyindoles: an enabling, yet understated progeny of vinylogous carbon nucleophiles. European Journal of Organic Chemistry, Vol. 2012 (3), p. 466-470. eISSN 1099-0690. Article.

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DOI: 10.1002/ejoc.201101446

Abstract

We introduce novel 3-alkenyl-2-silyloxyindole nucleophiles and demonstrate their utility by developing an unprecedented vinylogous Mukaiyama-type aldol reaction with aromatic aldehydes. This reaction displays excellent levels of γ- site selectivity and diastereoselectivity and delivers valuable hydroxylated oxindoles bearing a substituted exocyclic double bond at the C-3 position. A preliminary trial of an asymmetric, catalytic version was conducted, and it showed promising enantioselectivity for the desired vinylogous aldol products.

Item Type:Article
ID Code:6922
Status:Published
Refereed:Yes
Uncontrolled Keywords:Aldol reactions, asymmetric catalysis, nitrogen heterocycles, silicon, nucleophiles
Subjects:Area 03 - Scienze chimiche > CHIM/03 Chimica generale e inorganica
Divisions:002 Altri enti e centri di ricerca del Nord Sardegna > CNR-Consiglio Nazionale delle Ricerche > Istituto di chimica biomolecolare, Sassari
Publisher:Wiley
eISSN:1099-0690
Deposited On:03 Jan 2012 14:14

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