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.
Uncatalyzed, Diastereoselective Vinylogous Mukaiyama Aldol Reactions on Aqueous Media: Pyrrole vs Furan 2-Silyloxy Dienes / Curti, Claudio; Battistini, Lucia; Zanardi, Franca; G., Rassu; V., Zambrano; L., Pinna; Casiraghi, Giovanni. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - 75:(2010), pp. 8681-8684. [10.1021/jo101799e]
Uncatalyzed, Diastereoselective Vinylogous Mukaiyama Aldol Reactions on Aqueous Media: Pyrrole vs Furan 2-Silyloxy Dienes
CURTI, Claudio;BATTISTINI, Lucia;ZANARDI, Franca;CASIRAGHI, Giovanni
2010-01-01
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.| File | Dimensione | Formato | |
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