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Updated: Jan 16, 2026
![Solid-phase Synthesis of [4.4] Spirocyclic Oximes](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F58508.jpg&w=3840&q=50)
Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
An Axle-Cycle Induction Strategy for the Synthesis of Chiral [2]Rotaxanes
Ranran Wang1, Conghao Shi1, Wang Xie1
1State Key Laboratory of Analytical Chemistry for Life Science, Jiangsu Key Laboratory of Advanced Organic Materials, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210023, China.
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.
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