Enantioselective Synthesis of Chiral Indane Derivatives by Rhodium-Catalyzed Addition of Arylboron Reagents to Substituted Indenes.

Rhodium-catalyzed asymmetric addition of arylboron reagents to indene derivatives proceeded to give 2-arylindanes in good yields with high enantioselectivity. Deuterium-labeling experiments indicated that the present reaction involved a 1,4-Rh shift from an initially formed benzylrhodium to an arylrhodium intermediate before protonation leading to the corresponding addition product. The asymmetric addition was also successful for acenaphthylene, which has a similar skeleton to indene, where it was found that the benzylrhodium intermediate underwent direct protonation without the 1,4-Rh shift.