Literature DB >> 29796501

Chirality in rotaxanes and catenanes.

E M G Jamieson1, F Modicom, S M Goldup.   

Abstract

Although chiral mechanically interlocked molecules (MIMs) have been synthesised and studied, enantiopure examples are relatively under-represented in the pantheon of reported catenanes and rotaxanes and the underlying chirality of the system is often even overlooked. This is changing with the advent of new applications of MIMs in catalysis, sensing and materials and the appearance of new methods to access unusual stereogenic units unique to the mechanical bond. Here we discuss the different stereogenic units that have been investigated in catenanes and rotaxanes, examples of their application, methods for assigning absolute stereochemistry and provide a perspective on future developments.

Entities:  

Year:  2018        PMID: 29796501      PMCID: PMC6049620          DOI: 10.1039/c8cs00097b

Source DB:  PubMed          Journal:  Chem Soc Rev        ISSN: 0306-0012            Impact factor:   54.564


  148 in total

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Authors:  Jean-François Ayme; Jonathon E Beves; David A Leigh; Roy T McBurney; Kari Rissanen; David Schultz
Journal:  Nat Chem       Date:  2011-11-06       Impact factor: 24.427

2.  A chiral [2]catenane self-assembled from meso-macrocycles of palladium(II).

Authors:  Tara J Burchell; Dana J Eisler; Richard J Puddephatt
Journal:  Dalton Trans       Date:  2004-12-10       Impact factor: 4.390

Review 3.  Asymmetric enamine catalysis.

Authors:  Santanu Mukherjee; Jung Woon Yang; Sebastian Hoffmann; Benjamin List
Journal:  Chem Rev       Date:  2007-12       Impact factor: 60.622

4.  A new doubly interlocked [2]catenane.

Authors:  Carlos Peinador; Víctor Blanco; José M Quintela
Journal:  J Am Chem Soc       Date:  2009-01-28       Impact factor: 15.419

5.  Self-assembly of a giant molecular Solomon link from 30 subcomponents.

Authors:  Clément Schouwey; Julian J Holstein; Rosario Scopelliti; Konstantin O Zhurov; Konstantin O Nagornov; Yury O Tsybin; Oliver S Smart; Gérard Bricogne; Kay Severin
Journal:  Angew Chem Int Ed Engl       Date:  2014-08-28       Impact factor: 15.336

Review 6.  Cyclodextrin-based molecular machines.

Authors:  A Harada
Journal:  Acc Chem Res       Date:  2001-06       Impact factor: 22.384

Review 7.  The Art of Building Small: From Molecular Switches to Motors (Nobel Lecture).

Authors:  Ben L Feringa
Journal:  Angew Chem Int Ed Engl       Date:  2017-07-27       Impact factor: 15.336

8.  Enantiodifferentiation in the Photoisomerization of (Z,Z)-1,3-Cyclooctadiene in the Cavity of γ-Cyclodextrin-Curcubit[6]uril-Wheeled [4]Rotaxanes with an Encapsulated Photosensitizer.

Authors:  Zhiqiang Yan; Qinfei Huang; Wenting Liang; Xingke Yu; Dayang Zhou; Wanhua Wu; Jason J Chruma; Cheng Yang
Journal:  Org Lett       Date:  2017-01-30       Impact factor: 6.005

9.  Goldberg Active Template Synthesis of a [2]Rotaxane Ligand for Asymmetric Transition-Metal Catalysis.

Authors:  Steven Hoekman; Matthew O Kitching; David A Leigh; Marcus Papmeyer; Diederik Roke
Journal:  J Am Chem Soc       Date:  2015-06-16       Impact factor: 15.419

10.  Tetrameric cyclic double helicates as a scaffold for a molecular Solomon link.

Authors:  Jonathon E Beves; Christopher J Campbell; David A Leigh; Robin G Pritchard
Journal:  Angew Chem Int Ed Engl       Date:  2013-05-06       Impact factor: 15.336

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  28 in total

1.  Mechanically axially chiral catenanes and noncanonical mechanically axially chiral rotaxanes.

Authors:  John R J Maynard; Peter Gallagher; David Lozano; Patrick Butler; Stephen M Goldup
Journal:  Nat Chem       Date:  2022-06-27       Impact factor: 24.274

2.  A Co-conformationally "Topologically" Chiral Catenane.

Authors:  Arnau Rodríguez-Rubio; Andrea Savoini; Florian Modicom; Patrick Butler; Stephen M Goldup
Journal:  J Am Chem Soc       Date:  2022-06-28       Impact factor: 16.383

Review 3.  Rotaxane nanomachines in future molecular electronics.

Authors:  Peiqiao Wu; Bhushan Dharmadhikari; Prabir Patra; Xingguo Xiong
Journal:  Nanoscale Adv       Date:  2022-06-24

Review 4.  BINOL as a chiral element in mechanically interlocked molecules.

Authors:  Matthias Krajnc; Jochen Niemeyer
Journal:  Beilstein J Org Chem       Date:  2022-05-06       Impact factor: 2.544

5.  Metastable doubly threaded [3]rotaxanes with a large macrocycle.

Authors:  Jerald E Hertzog; Vincent J Maddi; Laura F Hart; Benjamin W Rawe; Phillip M Rauscher; Katie M Herbert; Eric P Bruckner; Juan J de Pablo; Stuart J Rowan
Journal:  Chem Sci       Date:  2022-04-20       Impact factor: 9.969

6.  CB[7]- and CB[8]-Based [2]-(Pseudo)rotaxanes with Triphenylphosphonium-Capped Threads: Serendipitous Discovery of a New High-Affinity Binding Motif.

Authors:  Iago Neira; Carlos Peinador; Marcos D García
Journal:  Org Lett       Date:  2022-05-06       Impact factor: 6.072

7.  Anion-π Catalysis Enabled by the Mechanical Bond.

Authors:  John R J Maynard; Bartomeu Galmés; Athanasios D Stergiou; Mark D Symes; Antonio Frontera; Stephen M Goldup
Journal:  Angew Chem Int Ed Engl       Date:  2022-02-03       Impact factor: 16.823

8.  Selective synthesis and structural transformation between a molecular ring-in-ring architecture and an abnormal trefoil knot.

Authors:  Li-Long Dang; Xiang Gao; Yue-Jian Lin; Guo-Xin Jin
Journal:  Chem Sci       Date:  2020-07-15       Impact factor: 9.825

9.  Diastereoselective synthesis of [1]rotaxanes via an active metal template strategy.

Authors:  Noël Pairault; Adrien Bessaguet; Romain Barat; Lucas Frédéric; Grégory Pieters; Jeanne Crassous; Isabelle Opalinski; Sébastien Papot
Journal:  Chem Sci       Date:  2020-12-29       Impact factor: 9.825

10.  Spin-labelled mechanically interlocked molecules as models for the interpretation of biradical EPR spectra.

Authors:  Lorenzo Gualandi; Paola Franchi; Elisabetta Mezzina; Stephen M Goldup; Marco Lucarini
Journal:  Chem Sci       Date:  2021-05-14       Impact factor: 9.825

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