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Solvent-free Mukaiyama and Mukaiyama–Michael vinylogous reactions of a dioxinone-derived silyl enol ether promoted by Lewis bases

Scettri, Arrigo and De Sio, Vincenzo and Villano, Rosaria and Manzo, Patrizia and Acocella, Maria Rosaria (2010) Solvent-free Mukaiyama and Mukaiyama–Michael vinylogous reactions of a dioxinone-derived silyl enol ether promoted by Lewis bases. Tetrahedron Letters, Vol. 51 (28), p. 3658-3661. ISSN 0040-4039. Article.

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DOI: 10.1016/j.tetlet.2010.05.016

Abstract

The vinylogous aldol-type addition of a dienolsilyl ether, derived from 2,2,6-trimethyl-4H-1,3-dioxin-4-one, showed to occur with complete γ-selectivity by enolate activation promoted by neutral Lewis bases under solvent-free conditions. Moderate to high yields were obtained with aromatic, hetero-aromatic, and aliphatic aldehydes, as well as activated ketones. Under the same conditions and in the absence of catalyst, the first Mukaiyama–Michael addition of the masked acetoacetate ester to α,β-unsaturated aldehydes took place in satisfactory way.

Item Type:Article
ID Code:5606
Status:Published
Refereed:Yes
Uncontrolled Keywords:Mukaiyama, Mukaiyama–Michael, dioxinone, vinylogous, aldol reaction
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:Pergamon / Elsevier
ISSN:0040-4039
Copyright Holders:© 2010 Elsevier
Deposited On:09 Mar 2011 13:54

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