Synthesis of multifunctionalized building blocks via vinylogous addition of Chan’s diene to carbonyl and carbonyl-related electrophiles, mediated by molecular iodine |
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| Authors: | Rosaria Villano Maria R AcocellaArrigo Scettri |
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| Institution: | a Istituto di Chimica Biomolecolare—CNR, Trav. La Crucca 3, Reg. Baldinca, 07040 Li Punti, Sassari, Italy
b Dipartimento di Chimica, Università di Salerno, via Ponte don Melillo, 84084 Fisciano, Salerno, Italy |
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| 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. |
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| Keywords: | Chan&rsquo s diene Vinylogous reaction Iodine δ-Functionalized β-ketoesters γ-Selectivity Catalysis |
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