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Uncatalyzed, diastereoselective vinylogous Mukaiyama aldol reactions on aqueous media: pyrrole vs furan 2-silyloxy dienes

Curti, Claudio and Battistini, Lucia and Zanardi, Franca and Rassu, Gloria Maria Rita and Zambrano, Vincenzo and Pinna, Luigi and Casiraghi, Giovanni (2010) Uncatalyzed, diastereoselective vinylogous Mukaiyama aldol reactions on aqueous media: pyrrole vs furan 2-silyloxy dienes. The Journal of Organic Chemistry, Vol. 75 (24), p. 8681-8684. eISSN 1520-6904. Article.

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DOI: 10.1021/jo101799e

Abstract

The first uncatalyzed, diastereoselective vinylogous Mukaiyama aldol reaction is reported, between pyrrole/furan-based dienoxy silanes and aromatic aldehydes on salty water/methanol medium, at almost human body temperature, under ultrasonic irradiation. With pyrrole dienes the reaction is anti-selective, while that of furan dienes is syn-selective. The dual role of water as both reaction medium and promoter is highlighted.

Item Type:Article
ID Code:5783
Status:Published
Refereed:Yes
Uncontrolled Keywords:Mukaiyama aldol, aqueous media, pyrrole, aromatic aldehydes
Subjects:Area 03 - Scienze chimiche > CHIM/06 Chimica organica
Divisions:001 Università di Sassari > 01 Dipartimenti > Chimica
002 Altri enti e centri di ricerca del Nord Sardegna > CNR-Consiglio Nazionale delle Ricerche > Istituto di chimica biomolecolare, Sassari
Publisher:American Chemical Society
eISSN:1520-6904
Deposited On:11 May 2011 09:04

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