A versatile, readily accessible triad of 2-enoxy silane synthons derived from furan, pyrrole, and thiophene is presented. These heterocycles, in reacting with carbonyl and carbonyl-related acceptors, act as vinylogous nucleophile modules, giving rise to diverse, functionality-rich, γ-substituted α,β-unsaturated carbonyl constructs. These, in turn, are invaluable platforms onto which further functional elements and chirality may be introduced. A couple of appealing applications-the variable construction of a repertoire of carbasugars and a library of annonaceous acetogenin segments-have been chosen to illustrate the viability of this vinylogous aldol approach.
Vinylogous aldol reaction of heterocyclic silyloxy dienes. Application in synthesis / Casiraghi, G.; Zanardi, F.; Rassu, G.. - In: PURE AND APPLIED CHEMISTRY. - ISSN 0033-4545. - 72:9(2000), pp. 1645-1648. [10.1351/pac200072091645]
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