A formal [3 + 3] cycloaddition reaction. Improved reactivity using alpha,beta-unsaturated iminium salts and evidence for reversibility of 6pi-electron electrocyclic ring closure of 1-oxatrienes |
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| Authors: | Shen Hong C Wang Jiashi Cole Kevin P McLaughlin Michael J Morgan Christopher D Douglas Christopher J Hsung Richard P Coverdale Heather A Gerasyuto Aleksey I Hahn Juliet M Liu Jia Sklenicka Heather M Wei Lin-Li Zehnder Luke R Zificsak Craig A |
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| Institution: | Department of Chemistry, University of Minnesota, Minneapolis, Minnesota 55455, USA. |
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| Abstract: | A detailed account regarding a formal 3 + 3] cycloaddition method using 4-hydroxy-2-pyrones and 1,3-diketones is described here. This formal cycloaddition reaction or annulation reaction is synthetically useful for constructing 2H-pyranyl heterocycles. The usage of alpha,beta-unsaturated iminium salts is significant in controlling competing reaction pathways to give exclusively 2H-pyrans. Most significantly, experimental evidence is provided to support the mechanism of this reaction that involves a sequential Knoevenagel condensation and a reversible 6pi-electron electrocyclic ring-closure of 1-oxatrienes. |
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