Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 83, Issue 20, Pages 12931-12938Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.8b01997
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- American Chemical Society Petroleum Research Fund [55852-UR1]
- University of Richmond Department of Chemistry
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Ketones readily undergo conversion to enol silanes in the presence of a trialkylamine base and trimethylsilyl trifluoromethanesulfonate (TMSOTf) and add to propargyl cations to yield beta-alkynyl ketones. The propargyl cations are generated in the same reaction flask through the TMSOTf-promoted ionization of propargyl acetates or propargyl propionates. A range of enol silane precursors and propargyl carboxylates reacts efficiently (20 examples, up to 99% yield). Cyclization of a representative product in the presence of TMSOTf provided 61% yield of the trisubstituted furan.
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