CrossRef enabled

PAC Archives

Archive →

Pure Appl. Chem., 2000, Vol. 72, No. 9, pp. 1645-1648

Vinylogous aldol reaction of heterocyclic silyloxy dienes. Application in synthesis

Giovanni Casiraghi, Franca Zanardi and Gloria Rassu

Dipartimento Farmaceutico dell'Università, I-43100 Parma, Italy and Istituto per l'Applicazione delle Tecniche Chimiche Avanzate ai Problemi Agrobiologici del CNR, I-07100 Sassari, Italy

Abstract: 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.