A Formal [3 + 3] Cycloaddition Reaction. Improved Reactivity Using α,β-Unsaturated Iminium Salts and Evidence for Reversibility of 6π-Electron Electrocyclic Ring Closure of 1-Oxatrienes
The Journal of Organic Chemistry2003Vol. 68(5), pp. 1729–1735
Citations Over TimeTop 10% of 2003 papers
Hong C. Shen, Jiashi Wang, Kevin P. Cole, Mike J. McLaughlin, Christopher D. Morgan, Christopher J. Douglas, Richard P. Hsung, H.A. Coverdale, Aleksey I. Gerasyuto, Juliet M. Hahn, Jia Liu, Heather M. Sklenicka, Lin-Li Wei, Luke R. Zehnder, Craig A. Zificsak
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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