Strategies for the Synthesis of Mechanically Planar Chiral Rotaxanes
- PMID: 40217105
- DOI: 10.1002/chem.202500898
Strategies for the Synthesis of Mechanically Planar Chiral Rotaxanes
Abstract
Rotaxanes, belonging to the class of classical mechanically interlocked molecules (MIMs), exhibit chiral properties that diverge from those of traditional chiral elements, particularly displaying mechanically planar chirality. Their distinctive spatial structure further augments their chiral significance, thereby imparting them with vast potential for applications in the realm of chiral materials and asymmetric catalysis. In recent years, mechanically planar chiral rotaxanes have garnered increasing attention from researchers. In this review, we summarize the recent advancements in obtaining enantiopure mechanically planar chiral rotaxanes. In this regard, chiral separation techniques, the use of chiral auxiliaries, and asymmetric catalytic synthesis have emerged as potent methodologies for constructing chiral rotaxanes, thereby enabling the synthesis of diverse types of mechanically planar chiral rotaxanes. Additionally, we analyze the current challenges faced in this field and look forward to the future development opportunities that lie ahead.
Keywords: asymmetric synthesis; mechanically planar chiral rotaxanes.
© 2025 Wiley‐VCH GmbH.
Similar articles
-
BINOL as a chiral element in mechanically interlocked molecules.Beilstein J Org Chem. 2022 May 6;18:508-523. doi: 10.3762/bjoc.18.53. eCollection 2022. Beilstein J Org Chem. 2022. PMID: 35601990 Free PMC article. Review.
-
Induction of Single-Handed Helicity of Polyacetylenes Using Mechanically Chiral Rotaxanes as Chiral Sources.Angew Chem Int Ed Engl. 2017 Nov 20;56(47):14858-14862. doi: 10.1002/anie.201707926. Epub 2017 Oct 18. Angew Chem Int Ed Engl. 2017. PMID: 28973787
-
Enantioselective preparation of mechanically planar chiral rotaxanes by kinetic resolution strategy.Nat Commun. 2021 Jan 15;12(1):404. doi: 10.1038/s41467-020-20372-0. Nat Commun. 2021. PMID: 33452235 Free PMC article.
-
Single-Step Enantioselective Synthesis of Mechanically Planar Chiral [2]Rotaxanes Using a Chiral Leaving Group Strategy.J Am Chem Soc. 2020 May 27;142(21):9803-9808. doi: 10.1021/jacs.0c03447. Epub 2020 May 13. J Am Chem Soc. 2020. PMID: 32356978 Free PMC article.
-
Chirality in rotaxanes and catenanes.Chem Soc Rev. 2018 Jul 17;47(14):5266-5311. doi: 10.1039/c8cs00097b. Chem Soc Rev. 2018. PMID: 29796501 Free PMC article. Review.
References
-
- a) J. E. Beves, B. A. Blight, C. J. Campbell, D. A. Leigh, R. T. McBurney, Angew. Chem. Int. Ed. 2011, 50, 9260;
-
- b) R. S. Forgan, J.‐P. Sauvage, J. F. Stoddart, Chem. Rev. 2011, 111, 5434;
-
- c) A. Coskun, M. Banaszak, R. D. Astumian, J. F. Stoddart, B. A. Grzybowski, Chem. Soc. Rev. 2012, 41, 19;
-
- d) N. H. Evans, P. D. Beer, Chem. Soc. Rev. 2014, 43, 4658;
-
- e) E. A. Neal, S. M. Goldup, Chem. Commun. 2014, 50, 5128;
Publication types
Grants and funding
LinkOut - more resources
Full Text Sources