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  • Title: Carbolithiation for the generation of cyclooctadienyl anions and tandem electrocyclization/alkylation to functionalized cis-bicyclo[3.3.0]octenes.
    Author: Williams DR, Reeves JT.
    Journal: J Am Chem Soc; 2004 Mar 24; 126(11):3434-5. PubMed ID: 15025465.
    Abstract:
    A powerful cascade reaction process for the construction of functionalized cis-bicyclo[3.3.0]octenes has been developed. Carbolithiation of 3-methylene-1,4-cyclooctadiene with 1 degrees , 2 degrees , or 3 degrees alkyllithium reagents leads to cyclooctadienyl anions, which undergo disrotatory electrocyclization and subsequent trapping with carbon, oxygen, sulfur, or silicon electrophiles to provide functionalized cis-bicyclo[3.3.0]octenes. Transmetalation of the allyllithium intermediates allowed access to the cuprate manifold of reactivity. The rapid construction of a linear triquinane using this methodology demonstrates the potential for synthetic applications.
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