Casiraghi, Giovanni and Zanardi, Franca and Rassu, Gloria Maria Rita (2000) Vinylogous aldol reaction of heterocyclic silyloxy dienes. Application in synthesis. Pure and Applied Chemistry, Vol. 72 (9), p. 1645-1648. eISSN 1365-3075. Article.
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.
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