From Center-to-Multilayer Chirality: Asymmetric Synthesis of Multilayer Targets with Electron-Rich Bridges

• Published in: Journal of organic chemistry Vol. 87; no. 9; pp. 5976 - 5986
• Main Authors: Tang, Yao, Wu, Guanzhao, Jin, Shengzhou, Liu, Yangxue, Ma, Liulei, Zhang, Sai, Rouh, Hossein, Ali, Ahmed I. M, Wang, Jia-Yin, Xu, Ting, Unruh, Daniel, Surowiec, Kazimierz, Li, Guigen
• Format: Journal Article
• Language: English
• Published: United States American Chemical Society 06-05-2022
• Subjects: Electrons; Stereoisomerism
• ISSN: 0022-3263; 1520-6904
• DOI: 10.1021/acs.joc.2c00234

Asymmetric synthesis of new atropisomerically multilayered chiral targets has been achieved by taking advantage of the strategy of center-to-multilayer chirality and double Suzuki–Miyaura couplings. Diastereomers were readily separated via flash column chromatography and well characterized. Absolute configuration assignment was determined by X-ray structural analysis. Five enantiomerically pure isomers possessing multilayer chirality were assembled utilizing anchors involving electron-rich aromatic connections. An overall yield of 0.69% of the final target with hydroxyl attachment was achieved over 11 steps from commercially available starting materials.