An enantioselective synthesis of functionalized cyclohepta­[b]­indoles via Pd-catalyzed cyclopropane C–H activation followed by olefination and indole–vinylcyclopropane rearrangement is reported. The design of the chiral cyclopropane precursor was such that both enantiomeric cyclohepta­[b]­indoles were accessed from a single compound exhibiting a “hidden” symmetry plane. The scope of the method was demonstrated by varying the substituents on the cyclopropane as well as on the heterocycle itself.