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,
g-substituted a,b-unsaturated
carbonyl constructs. These, in turn, are invaluable platforms onto which
further functional elements and chirality may be introduced. A couple
of appealing applicationsthe variable construction of a repertoire
of carbasugars and a library of annonaceous acetogenin segmentshave
been chosen to illustrate the viability of this vinylogous aldol approach.
*Lecture presented at the 13th International
Conference on Organic Synthesis (ICOS-13), Warsaw, Poland, 1-5 July
2000.
** Corresponding author
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