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

Hong C. Shen, Jiashi Wang, Kevin P. Cole, Michael J. McLaughlin, Christopher D. Morgan, Christopher J. Douglas, Richard P. Hsung, Heather A. Coverdale, Aleksey I. Gerasyuto, Juliet M. Hahn, Jia Liu, Heather M. Sklenicka, Lin Li Wei, Luke R. Zehnder, Craig A. Zificsak

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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 α,β-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 6π-electron electrocyclic ring-closure of 1-oxatrienes.

Original languageEnglish (US)
Pages (from-to)1729-1735
Number of pages7
JournalJournal of Organic Chemistry
Volume68
Issue number5
DOIs
StatePublished - Mar 7 2003

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