期刊
TETRAHEDRON
卷 62, 期 33, 页码 7762-7771出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2006.05.064
关键词
1,2-disubstituted cyclopropanol; Cu(NO3)(2); alpha-methyl-gamma-diketone; 2,3,5-trisubstituted furans
The ring-opening reaction of 1,2-di substituted cyclopropanols, prepared from beta-diketones, mediated by Cu(NO3)(2), p-TsOH, and NaOH is reported. The Cu(II)-mediated ring-opening of cyclopropanols gave alpha-methylene-gamma-diketones in good yields. The reaction took place at the less substituted carbon of the cyclopropanols, involving mild conditions and a simple procedure. The reaction induced by p-TsOH in CH2O2 afforded alpha-methyl-gamma-diketones as the major product with minor amounts of 8-diketones. The 2,3,5-tri substituted furans were obtained in high yields when the ring-opening reaction was mediated by p-TsOH in methanol under reflux conditions. In the presence of sodium hydroxide the reaction proceeded smoothly in preference to the formation of beta-diketones, particularly for substrates with an aromatic group on the cyclopropane. (c) 2006 Elsevier Ltd. All rights reserved.
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