Research Progress in Mechanically Chiral Rotaxanes

doi:10.6023/cjoc202504033

Abstract

Mechanically chiral rotaxanes, as a critical subclass of mechanically interlocked molecules (MIMs), demonstrate broad application prospects in molecular machines and asymmetric catalysis due to their unique stereochemical properties induced by mechanical bonds. Based on the symmetry feature of their components, mechanical chirality of rotaxanes is classified into three categories: mechanically planar chirality, mechanically axial chirality, and mechanical point-chirality. The stereochemical features of these three types are elucidated by analyzing the symmetry planes of each achiral macrocycle and axle, and then combining these two components. Currently, the preparation of mechanically chiral rotaxanes mainly relies on diastereoselective strategies employing chiral pools or chiral auxiliaries. A limited number of catalytic enantioselective synthesis of mechanically planar chiral and mechanically point-chiral rotaxanes have also been reported. This review systematically summarizes the current status and future directions in the field, categorized by the types of rotaxane chirality and their corresponding synthetic strategies. Application of mechanically chiral rotaxanes is also briefly introduced.

Key words: rotaxane, mechanically planar chirality, mechanically axial chirality, symmetry plane, asymmetric synthesis

Cite this article

Zhu Ruiqing, Zhu Ting, Wang Chao, Zong Lili. Research Progress in Mechanically Chiral Rotaxanes[J]. Chinese Journal of Organic Chemistry, doi: 10.6023/cjoc202504033.

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