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Synthesis of multifunctionalized building blocks via vinylogous addition of Chan’s diene to carbonyl and carbonyl-related electrophiles, mediated by molecular iodine

Villano, Rosaria and Acocella, Maria Rosaria and Scettri, Arrigo (2011) Synthesis of multifunctionalized building blocks via vinylogous addition of Chan’s diene to carbonyl and carbonyl-related electrophiles, mediated by molecular iodine. Tetrahedron, Vol. 67 (15), p. 2768-2772. eISSN 1464-5416. Article.

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DOI: 10.1016/j.tet.2011.02.036

Abstract

The synthesis of multifunctionalized β-ketoesters has been achieved by using molecular iodine as a catalyst under very mild conditions. The vinylogous addition of Chan’s diene 1 to carbonyl and carbonyl-related compounds (aldehydes, ketones, imines and acetals) occurred with high efficiencies and with complete γ-selectivity, giving a useful method for the synthesis of interesting libraries of different δ-functionalized β-ketoesters.

Item Type:Article
ID Code:5739
Status:Published
Refereed:Yes
Uncontrolled Keywords:Chan’s diene, vinylogous reaction, Iodine, δ-functionalized β-ketoesters, γ-selectivity, catalysis
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:Elsevier Science
eISSN:1464-5416
Deposited On:26 May 2011 09:59

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