Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 360, Issue 15, Pages 2938-2944Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201800551
Keywords
iodide catalysts; cyclopropanes; ring opening; cyclization; benzofurans
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Funding
- Japan Society for the Promotion of Science (JSPS) [JP15K07853]
- JSPS Core-to-Core Program, B. Asia-Africa Science Platforms
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The ring-opening cyclization of 2',3'-nonsubstituted and 2'-electron-withdrawing group (EWG)-substituted cyclohexane-1,3-dione-2-spirocyclopropanes was accomplished using iodide as a catalyst. The nonsubstituted derivatives afforded 3,5,6,7-tetrahydro-1-benzofuran-4(2H)-ones in high yields in the presence of trimethylsilyl iodide at room temperature. The EWG-substituted spirocyclopropanes, in turn, underwent regioselective ring opening followed by cyclization, which gave rise to 2-substituted tetrahydrobenzofuran-4-ones when a combination of tetrabutylammonium iodide catalyst and trifluoromethanesulfonic acid was used, whereas calcium iodide afforded the 3-substituted derivatives.
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