Core Viewpoint - The article discusses the advancements in the field of medium-sized rings (MSR) with a focus on non-traditional chiral types, including axial chirality, inherent chirality, and planar chirality, highlighting their synthesis strategies and stability factors [1][5]. Group 1: Overview of Medium-Sized Rings - Medium-sized rings (MSR) consist of 7-11 atoms and exhibit a unique "rigid-flexible" characteristic, making them significant in drug chemistry and functional materials [1]. - The review published by researchers from Zhengzhou University in Nature Reviews Chemistry emphasizes the importance of exploring non-traditional chiral MSRs, which have not been extensively studied compared to traditional central chirality [3][5]. Group 2: Types of Non-Traditional Chirality - Axial Chirality: This type arises from restricted rotation around a non-covalent bond axis, often constructed through dynamic kinetic resolution or asymmetric catalysis [4]. - Inherent Chirality: This chirality originates from the asymmetry of the ring framework itself, typically synthesized via cyclization reactions or template-directed methods [4]. - Planar Chirality: This involves the asymmetric arrangement of substituents within a molecular plane, requiring steric hindrance or ligand control for selective synthesis [4]. Group 3: Progress and Evaluation - The past decade has seen rapid advancements in the synthesis and application of non-traditional chiral MSRs, with significant breakthroughs reported [5]. - The review critically evaluates the key synthesis strategies for these chiral types and discusses the factors influencing the conformational stability of chiral medium-sized rings through structural and energy analysis [5].