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  • Title: Eight-membered ring construction by [4 + 2 + 2] annulation involving beta-carbon elimination.
    Author: Murakami M, Ashida S, Matsuda T.
    Journal: J Am Chem Soc; 2006 Feb 22; 128(7):2166-7. PubMed ID: 16478142.
    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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