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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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.
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