Stereodivergent Cyclopropanation of Alkenes with N-Enoxyphthalimides via C-H Activation

Abstract

A rhodium(III)-catalyzed cyclopropanation of alkenes with N-enoxyphthalimides, the imide moiety of which works as an oxidizing directing group for C-H activation, has been developed. Careful tuning of reaction conditions such as the N-enoxyphthalimides, ligands, and bases lead to stereodivergent results. The reaction mechanism including the stereoselectivity was discussed through detailed control experiments and multivariate analysis. This protocol has also been applied to cis-selective cyclopropanation of allyl alcohols. These approaches provide various cyclopropanes not accessible by other routes.