There is significant interest in the development of C-C bond-forming methodologies that directly access challenging benzylic stereocenters. Predominantly, efforts have been focused on the development of enantiospecific or enantioselective cross-coupling methodologies. An alternate and conceptually ideal approach involves the development of branch-selective and enantioselective Murai-type alkene hydroarylations. Recent progress towards this broad, yet challenging goal is highlighted.