New chiral targets of orientational chirality have been designed and asymmetrically synthesized by taking advantage of N-sulfinylimine-directed nucleophilic addition/oxidation, Suzuki-Miyaura and Sonogashira cross-coupling reactions. Orientation of single isomers has been selectively controlled by using aryl/alkynyl levers [C(sp2)-C(sp) axis] and tBuSO2- protecting group on nitrogen as proven by X-ray diffraction analysis. The key structural characteristic of resulting orientational products is shown by remote through-space blocking manner. seventeen examples of multi-step synthesis were obtained in modest to good chemical yields and complete orientational selectivity.