Enantioselective Synthesis of Inherently Chiral Tetraphenylene Analogues Enabled by NHC‐Catalyzed Benzoin Condensation
Abstract
ABSTRACT Herein, we report an enantioselective N‐heterocyclic carbene (NHC)‐catalyzed intramolecular benzoin reaction of bisaldehydes featuring a 1,1′:2′,1′′‐terphenyl linkage to afford eight‐membered α‐hydroxy ketones in which six of the eight ring atoms are benzene carbons. The benzene‐rich framework is conformationally inflexible and thus inherently chiral, adopting a saddle‐shaped conformation. A variety of heteroaromatic‐ and naphthalene‐embedded tetraphenylene analogues were prepared enantioselectively by routine transformations of the α‐hydroxy ketone moiety. Density functional theory (DFT) calculations elucidate the reaction mechanism and provide insights into the origin of the stereoselectivity.
Article Details
Authors (8)
Yuanhang Zhang
College of Environmental Sciences and Engineering, Peking University
Yu Luo
Macau Centre for Research and Development in Chinese Medicine, State Key Laboratory of Mechanism and Quality of Chinese Medicine, Institute of Chinese Medical Sciences
Tao Zhang
Meiling Chen
Yougen Xu
China‐New Zealand Belt and Road Joint Laboratory on Biomedicine and Health Guangzhou Institutes of Biomedicine and Health Chinese Academy of Sciences Guangzhou People's Republic of China
Guangwu Sun
Zhejiang Key Laboratory of New Drug Development for Central Nervous System Diseases, School of Pharmaceutical and Materials Engineering & Institute for Advanced Studies Taizhou University Taizhou Zhejiang People's Republic of China
Shuang Luo
Qiang Zhu
School of Science and Molecular Horizons, ARC Centre of Excellence in Quantum Biotechnology