A versatile procedure for the gamma-vinylogous aldol reaction of the dioxinone-derived silyl enolether, via enolate activation with an appropriate neutral Lewis base, was formulated. High levels of diastereo- and enantioselectivity using chiral 2-methylsulfinyl benzaldehyde were obtained, pointing out the dual role of the methylsulfinyl group as incorporated chiral inductor and activator of the silyloxydiene in the stereoselective vinylogous aldol reaction.

Vinylogous Aldol Reaction of a Silyloxydiene Promoted by Sulfoxides, as Lewis Bases: 1,4-asymmetric Induction Mediated by a Remote Methylsulfinyl Group

ACOCELLA, MARIA ROSARIA;COSTABILE, Chiara;
2013

Abstract

A versatile procedure for the gamma-vinylogous aldol reaction of the dioxinone-derived silyl enolether, via enolate activation with an appropriate neutral Lewis base, was formulated. High levels of diastereo- and enantioselectivity using chiral 2-methylsulfinyl benzaldehyde were obtained, pointing out the dual role of the methylsulfinyl group as incorporated chiral inductor and activator of the silyloxydiene in the stereoselective vinylogous aldol reaction.
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11386/3962604
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