Pan Ming, Shao Ying-Bo, Zhao Qun, Li Xin
State Key Laboratory of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, People's Republic of China.
Org Lett. 2022 Jan 14;24(1):374-378. doi: 10.1021/acs.orglett.1c04028. Epub 2021 Dec 20.
N-N axially chiral skeletons are significant structural motifs in natural products, pharmaceuticals, and functional materials. Herein we disclose a method for the asymmetric synthesis of N-N axially chiral compounds by phase-transfer catalysis. A wide range of N-N axially chiral quinazolinone derivatives were prepared in high yields with excellent stereoselectivities. Furthermore, the synthetic utility of the protocol was proved by large-scale reaction and transformation of the product. Density functional theory calculations provide insight into the mechanism.
N-N轴手性骨架是天然产物、药物和功能材料中重要的结构基序。在此，我们披露了一种通过相转移催化不对称合成N-N轴手性化合物的方法。以高产率和优异的立体选择性制备了多种N-N轴手性喹唑啉酮衍生物。此外，通过大规模反应和产物转化证明了该方法的合成实用性。密度泛函理论计算为反应机理提供了深入见解。
