A rhodium catalyzed ortho C-H activation/cyclization of enantiomerically enriched cyclic sulfamidates with activated alkenes for direct and highly efficient synthesis of trans-1,3-substituted isoindolines were described. With cyclic sulfamidate being a directing group (DG), the reaction proceeds through a tandem C-H activation and subsequent aza-Michael addition to deliver trans-1,3-disubstituted isoindolines exclusively with excellent enatio- and diastereoselectivity. In addition, high yield, broad range of substrate scope, and functional group tolerance make this process of great practicality. The mechanistic studies indicated that the catalytic cleavage of ortho C-H bond is not likely to be the rate determining step (KIE = 1.2). The utility of this methodology and the advantage of easily transformable cyclic sulfamidate group has been highlighted by the synthesis of 1,3-disubstituted isoindolines.