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Vinylogous aldol reaction of heterocyclic silyloxy dienes. Application in synthesis

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.

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DOI: 10.1351/pac200072091645


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.

Item Type:Article
ID Code:846
Uncontrolled Keywords:Vinylogy, aldol reaction, chirality, carbasugars
Subjects:Area 03 - Scienze chimiche > CHIM/06 Chimica organica
Divisions:002 Altri enti e centri di ricerca del Nord Sardegna > CNR-Consiglio Nazionale delle Ricerche > Istituto di chimica biomolecolare, Sassari
Publisher:International Union of Pure and Applied Chemistry
Publisher Policy:Depositato in conformità con la politica di copyright dell'Editore
Additional Information:Lecture presented at the 13. International conference on Organic synthesis (ICOS-13), Warsaw, Poland, 1-5 July 2000.
Deposited On:18 Aug 2009 10:03

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