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Pushing the boundaries of vinylogous reactivity: catalytic enantioselective mukaiyama aldol reactions of highly unsaturated 2-silyloxyindoles

Curti, Claudio and Sartori, Andrea and Battistini, Lucia and Brindani, Nicoletta and Rassu, Gloria Maria Rita and Pelosi, Giorgio and Lodola, Alessio and Mor, Marco and Casiraghi, Giovanni and Zanardi, Franca (2015) Pushing the boundaries of vinylogous reactivity: catalytic enantioselective mukaiyama aldol reactions of highly unsaturated 2-silyloxyindoles. Chemistry: a European Journal, Vol. 21 (17), p. 6433-6442. ISSN 0947-6539. Article.

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DOI: 10.1002/chem.201500083

Abstract

The first example of catalytic, enantioselective hypervinylogous Mukaiyama aldol reaction (HVMAR) involving multiply unsaturated 2-silyloxyindoles is reported. The reaction utilizes a chiral Lewis base-catalyzed Lewis acid-mediated technology to deliver homoallylic 3-polyenylidene 2-oxindoles with extraordinary levels of regio-, enantio-, and geometrical selectivity. This work highlights a subtle yet decisive influence of the indole N-substituents on the propagation of the vinylogous reactivity space of the donor substrates up to ten bonds away from the origin of the vinylogy effect. Analysis of the 13C NMR chemical shifts of the C-ω remote site within homologous silyloxyindole donors enabled rationalization of the results and easy qualitative prediction of the HVMAR reactivity/inertia toward a given aldehyde acceptor.

Item Type:Article
ID Code:10906
Status:Published
Refereed:Yes
Uncontrolled Keywords:Aldol reaction, amides, asymmetric synthesis, vinylogy, oxindoles
Subjects:Area 03 - Scienze chimiche > CHIM/06 Chimica organica
Divisions:002 Altri enti e centri di ricerca del Nord Sardegna > CNR-Consiglio Nazionale delle Ricerche > Istituto di chimica biomolecolare, Sassari
Publisher:Wiley
ISSN:0947-6539
Deposited On:25 May 2015 11:25

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