An Axle-Cycle Induction Strategy for the Synthesis of Chiral [2]Rotaxanes
Ranran Wang, Conghao Shi, Wang Xie, Yang Zhou, Shirong Ban, Guofeng Xu, Juli Jiang, Zhigang Ni, Xiaoqi Wang, Xiancai Lu, Yong Liang, Leyong Wang
Abstract
Chiral rotaxanes have attracted considerable attention due to their distinctive properties resulting from their unique mechanically interlocked structures. However, the construction of chiral rotaxanes based on the dynamic racemic pillar[5]arene ( DMP5A ) by induction remains uncharted territory. In this study, we provide a method for synthesizing chiral rotaxanes based on DMP5A via an axle-cycle induction strategy. Amino acid derivatives serve as both chiral axles and chiral inducers for DMP5A, enabling the diastereoselective construction of chiral [2]rotaxanes. This axle-cycle induction strategy not only offers a synthetic method for DMP5A -based chiral rotaxanes with stereochemical control but also provides a foundation for chiral stationary-phase high-performance liquid chromatography (HPLC)-free (CSP-free) synthesis of mechanically interlocked molecules.