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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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.
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