Cyclopentadienyl Rhodium(III) complexes are effective catalysts for C–H activation, providing access to various nitrogen containing heterocycles. However, limited studies exist on the ligand effect. Recently, we discovered N-enoxyphthalimides participate in a [2+1] annulation with electron deficient alkenes to form trans-disubstituted cyclopropanes. The design of a mono-substituted isopropylcyclopentadienyl ligand is crucial to the success of the reaction allowing high diastereoselectivity in favor of the trans adduct. Conversely, we found the diastereoinduction could be reversed. We discovered aryl-substituted cyclopentadienyl ligands enable access to the cis-diastereomer. Reference: Piou, T.; Rovis, T. J. Am. Chem. Soc. 2014, 136, 11292–11295.

Rh(III)-catalyzed cyclopropanation initiated by C-H activation: Using ligand design to direct diastereoselectivity

249th National Meeting (2015)

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