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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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.
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