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The Synthetic utility of furan-, pyrrole- and thiophene-based 2-silyloxy dienes

Rassu, Gloria Maria Rita and Zanardi, Franca and Battistini, Lucia and Casiraghi, Giovanni (2000) The Synthetic utility of furan-, pyrrole- and thiophene-based 2-silyloxy dienes. Chemical Society Reviews, Vol. 29 , p. 109-118. ISSN 0306-0012. eISSN 1460-4744. Article.

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DOI: 10.1039/A900200F

Abstract

The aim of this review is to highlight the utility of a remarkable triad of 2-silyloxy diene synthons derived from furan, pyrrole and thiophene in organic synthesis. These heterocycles, in reacting with a number of carbonyl-related compounds (aldehydes, imines, heteroatom-stabilized carbenium ions), act as vinylogous nucleophile modules giving rise to a myriad of functionality-rich aldol-type constructs. These, in turn, represent invaluable synthetic platforms onto which a limitless number of functional elements and chosen chirality may be introduced. Eleven syntheses, amongst the most appealing of 1991–1999, have been chosen to illustrate the potentiality of silyloxy diene chemistry.

Item Type:Article
ID Code:10741
Status:Published
Refereed:Yes
Uncontrolled Keywords:Furan, pyrrole, thiophene, organic synthesis
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
Publisher:Royal Society of Chemistry
ISSN:0306-0012
eISSN:1460-4744
Deposited On:03 Feb 2015 09:47

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