A Star of David [2]catenane of single handedness

作者：Feng, Hai-Na; Sun, Zhanhu; Chen, Sujun; Zhang, Zhi-Hui; Li, Zhiming; Zhong, Zhiye; Sun, Tu; Ma, Yanhang; Zhang, Liang^*

来源：Chem, 2023, 9(4).

DOI：10.1016/j.chempr.2022.11.010

• STEREOSELECTIVE-SYNTHESIS
• KNOTS
• TOPOLOGY
• LIGANDS
• WRITHE
• COMPLEXES
• CATENANES
• CHIRALITY
• THREADS
• RINGS

Prime links with multiple interlocked components feature uncondi-tional topological chirality. Although several prime links have been constructed to date, the control of their chirality with high stereoin-duction is rare. Here, we report the stereoselective synthesis of an iconic molecular 621 link (Star of David [2]catenane) comprising two triply entwined 84-membered rings. The single-handed Star of Da-vid catenane is generated from the closure of a hexameric copper(I) circular helicate by ring-closing olefin metathesis, and the topolog-ical writhe (w = -6) was predetermined by the configuration of the chiral ligand. Conformation of the topology was proven through NMR spectroscopy and mass spectrometry, whereas the handed-ness of the link was further investigated through circular dichroism. Stereoselective synthesis of molecular nanotopologies with certain topological writhe by chiral information transfer opens the way to probe the consequences and potential of topological stereochemis-try in chemistry, materials, and biology.

• 单位
  复旦大学