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

Chemistry. 2024 Mar 18:e202400005. doi: 10.1002/chem.202400005. Online ahead of print.ABSTRACTNew 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.PMID:38497560 | DOI:10.1002/chem.202400005

Source: Chemistry - March 18, 2024 Category: Chemistry Authors: Yu Wang Ting Xu Shengzhou Jin Jia-Yin Wang Qingkai Yuan Hao Liu Yao Tang Sai Zhang Guigen Li Source Type: research