A Dynamic Kinetic Resolution Approach to Axially Chiral Diaryl Ethers via Catalytic Atroposelective Transfer Hydrogenation.

作者：Linlong Dai, Yuheng Liu, Qinghua Xu, Meifang Wang, Qiaohong Zhu, Peiyuan Yu, Xiaofei Zeng, Guofu Zhong · 发表于：Angewandte Chemie · 年份：2022 · DOI：10.1002/ange.202216534 · 被引用次数：53 · 研究领域：Medicine

Diaryl ethers are widespread in biologically active compounds, ligands and catalysts. It is known that the diaryl ether skeleton may exhibit atropisomerism when both aryl rings are unsymmetrically substituted by steric hindered groups. Despite recent advances, only a very few catalytic asymmetric methods have been developed to construct such kind of axially chiral compounds. We described herein a dynamic kinetic resolution approach to axially chiral diaryl ethers via Brønsted acid catalyzed atroposelective transfer hydrogenation (ATH) reaction of dicarbaldehydes with anilines. The desired diaryl ethers could be obtained in moderate to good chemical yields (up to 79%) and high enantioselectivities (up to 95% ee) under standard reaction conditions. Such structural motifs are interesting precursors for further transformations and may have potential applications in synthesis of chiral ligands or catalysts.