Synthesis of Substituted Cyclooctenes through Cross-Coupling Reactions

Abstract Cross-coupling methods for the introduction of various substituents onto the olefin moiety of cyclooctenes were developed. A range of 1-substituted cis-cyclooctenes were synthesized. These protocols unlocked routes to previously inaccessible derivatives, permitting the syntheses of cis-cyclooctenes bearing various functional groups. Moreover, the method was applied to the synthesis of a 1,2-disubstituted trans-cyclooctene for the first time, which proved to be a significantly more active organocatalyst than the previously developed monosubstituted trans-cyclooctene.