Journal
CHINESE JOURNAL OF CHEMISTRY
Volume 35, Issue 8, Pages 1231-1238Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/cjoc.201600796
Keywords
double Michael reactions; spiro[benzofuran-2; 1'-cyclohexane]-3-one; spiro[cyclohexane-1; 2'-indene]-1'; 4(3'H)-dione; functional ionic liquids
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Funding
- Key Project of Science and Technology Research of the Education Department of Henan Province [15A150034]
- Fundamental Research Foundations for Provincial Colleges and Universities [zzjj20140006]
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The double Michael reactions between benzofuran-3-one or 1-indone and symmetric dienones in the presence of catalytic ionic liquids were successfully developed and spiro[benzofuran-2,1'-cyclohexane]-3-one or spiro[cyclohexane-1,2'-indene]-1',4(3'H)-dione derivatives containing a spiro quaternary stereogenic center, which widely exist in biologically active products and building blocks in organic synthesis, were obtained in excellent yields (up to 99%). This catalytic system was also extended to the double Michael reaction of less reactive 1-indone and the desired products were also obtained in 31%-62% yields. The catalytic system was highly active and efficient for a broad of substrates under mild conditions.
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