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.
2010
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]
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11381/2408151
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