Artikel
Design and Asymmetric Control of Orientational Chirality by using the Combination of C(sp2)‐C(sp) Levers and Achiral N‐Protecting Group
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.
