Wei Shengkai, Chen Liang-Yu, Li Junqi
Department of Chemistry, Iowa State University, Ames, Iowa 50011, United States.
Org Lett. 2025 Jul 4;27(26):7132-7136. doi: 10.1021/acs.orglett.5c02041. Epub 2025 Jun 22.
We report the design, synthesis, and characterization of achiral macrocyclic metacyclophanes exhibiting atropdiasteromerism. These macrocycles contain a 1,2,6-trisubstituted benzene in which the 1 position bears an amide group and the 2 and 6 positions are connected by a bridging chain. Because of the hindered rotation about the C(aryl)-C(acyl) bond and C(sp)-C(sp) bonds, the C═O bond of the amide group may be oriented toward or away from the interior of the macrocycle, resulting in observable and separable stereoisomers.
我们报道了具有阻转非对映异构现象的非手性大环间环芳烷的设计、合成及表征。这些大环包含一个1,2,6-三取代苯，其中1位带有一个酰胺基团，2位和6位通过一条桥链相连。由于围绕C(芳基)-C(酰基)键和C(sp)-C(sp)键的旋转受阻，酰胺基团的C═O键可朝向或远离大环内部，从而产生可观察到且可分离的立体异构体。
