Building on previous success using <i>N-</i>enoxyphthalimides for C–H functionalizations, a new method for highly diastereoselective cyclopropanation of allylic alcohols has been developed. The methodology is enabled by a directed Rh(III)-catalyzed alkenyl C–H activation of <i>N-</i>enoxyphthalimides followed by a [2+1] annulation to furnish substituted acylcyclopropanes with high levels of diastereoselectivity. Furthermore, the oxyphthalimide handle used as an oxidant is removed in the process acting as a traceless directing group. A new class of olefins are shown to be reactive coupling partners in the presence of a Rh(III) catalyst featuring an electron deficient cyclopentadienyl ligand that drastically improves yield and diastereoselectivity.

Rh(III)-catalyzed diastereoselective cyclopropanation of allylic alcohols initiated by C–H activation

255th National Meeting (2018)

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