Eight-membered ring construction by [4 + 2 + 2] annulation involving beta-carbon elimination |
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Authors: | Murakami Masahiro Ashida Shinji Matsuda Takanori |
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Institution: | Department of Synthetic Chemistry and Biological Chemistry, Kyoto University, Katsura, Kyoto 615-8510, Japan. murakami@sbchem.kyoto-u.ac.jp |
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Abstract: | Cyclobutanones underwent a formal 4 + 2 + 2] annulation reaction with 1,6- and 1,7-diynes in the presence of nickel(0) catalysts to provide bicyclic eight-membered ring ketones. The annulation reaction proceeds through a ring-expansion of oxanickelacycloheptadiene via beta-carbon elimination to form a nine-membered nickelacycle. This reaction employing cyclobutanones as a C4 unit constructs cyclooctadienone cores in one synthetic step. |
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