A chiral macrocycle for the stereoselective synthesis of mechanically planar chiral rotaxanes and catenanes

2023/02/15 by Shu Zhang, Arnau Rodríguez-Rubio, Abed Saady +2 · 1 voice · 3 citations
Biochemistry, Genetics and Molecular Biology · Chemistry · Engineering · #Chemical Synthesis and Analysis #Supramolecular Chemistry and Complexes #Surface Chemistry and Catalysis

paper · doi:10.1016/j.chempr.2023.01.009

openalex publication_date 2023/02/15 · openalex created_date 2025/10/10 · openalex updated_date 2026/08/01

Abstract

<h2>Summary</h2> Active template auxiliary methodologies have previously been developed for the stereoselective synthesis of chiral interlocked molecules in which the mechanical bond provides the sole stereogenic unit. To date, however, the covalent auxiliary has been included in the half-axle components (rotaxanes) or pre-macrocycle components (catenanes), and thus mechanically chiral rotaxane and catenane syntheses rely on different chiral components. Here, we present a single, simple amino-acid-derived macrocycle that mediates the formation of both catenanes and rotaxanes in excellent stereoselectivity. We demonstrate the flexibility of our approach through the stereoselective synthesis of all three isomers of a co-conformationally mechanically planar chiral [3]rotaxane.

Citations

• An Efficient Approach to Mechanically Planar Chiral Rotaxanes

Cited by

• Rotaxane synthesis via a dynamic [2]catenane-ring-opening, axle-cleaving double cross metathesis
• Metal‐Free Active Template Synthesis of Catenanes
• The End of the Beginning of Mechanical Stereochemistry

Discussions

• We have since made rotaxanes & catenanes stereoselectively (doi.org/10.1016/j.ch...), found new stereochemistry (doi.org/10.1038/s415...) & redefined mechanical stereochemistry theory (doi.org/10.1038 [bsky, 0 points, 1 comments]