The University of Southampton
University of Southampton Institutional Repository

Strategies for the synthesis of enantiopure mechanically chiral molecules

Strategies for the synthesis of enantiopure mechanically chiral molecules
Strategies for the synthesis of enantiopure mechanically chiral molecules
Mechanically interlocked molecules, such as rotaxanes and catenanes, are composed of two or more covalent subcomponents threaded through one another such that they cannot be separated without breaking a covalent bond. This arrangement can allow the covalent subcomponents to undergo large amplitude relative motion, and this property of the mechanical bond has been widely exploited in the design and synthesis of molecular machines. Another less well-known property of the mechanical bond is that it can give rise to chirotopic stereogenic units that do not rely on covalent stereogenic elements. Although the study of such "mechanically chiral" molecules is expanding, their synthesis in enantiopure form remains challenging. In this perspective we review the strategies available, highlighting key examples along the way, and suggest future areas for development.
chirality, rotaxanes, Catenanes, Stereoselective, Synthesis
2451-9308
1914-1932
Maynard, John Robert James
4e09e766-1294-4056-8bff-4277874f0495
Goldup, Stephen
0a93eedd-98bb-42c1-a963-e2815665e937
Maynard, John Robert James
4e09e766-1294-4056-8bff-4277874f0495
Goldup, Stephen
0a93eedd-98bb-42c1-a963-e2815665e937

Maynard, John Robert James and Goldup, Stephen (2020) Strategies for the synthesis of enantiopure mechanically chiral molecules. Chem, 6 (8), 1914-1932. (doi:10.1016/j.chempr.2020.07.012).

Record type: Article

Abstract

Mechanically interlocked molecules, such as rotaxanes and catenanes, are composed of two or more covalent subcomponents threaded through one another such that they cannot be separated without breaking a covalent bond. This arrangement can allow the covalent subcomponents to undergo large amplitude relative motion, and this property of the mechanical bond has been widely exploited in the design and synthesis of molecular machines. Another less well-known property of the mechanical bond is that it can give rise to chirotopic stereogenic units that do not rely on covalent stereogenic elements. Although the study of such "mechanically chiral" molecules is expanding, their synthesis in enantiopure form remains challenging. In this perspective we review the strategies available, highlighting key examples along the way, and suggest future areas for development.

Text
rvsd MS clean Maynard chiral chem perspective - Accepted Manuscript
Download (1MB)

More information

Accepted/In Press date: 14 July 2020
e-pub ahead of print date: 6 August 2020
Keywords: chirality, rotaxanes, Catenanes, Stereoselective, Synthesis

Identifiers

Local EPrints ID: 449977
URI: http://eprints.soton.ac.uk/id/eprint/449977
ISSN: 2451-9308
PURE UUID: 7a76eb94-8cc6-4f53-8444-a8b4a96971c7
ORCID for Stephen Goldup: ORCID iD orcid.org/0000-0003-3781-0464

Catalogue record

Date deposited: 01 Jul 2021 16:30
Last modified: 28 Apr 2022 04:16

Export record

Altmetrics

Contributors

Author: John Robert James Maynard
Author: Stephen Goldup ORCID iD

Download statistics

Downloads from ePrints over the past year. Other digital versions may also be available to download e.g. from the publisher's website.

View more statistics

Atom RSS 1.0 RSS 2.0

Contact ePrints Soton: eprints@soton.ac.uk

ePrints Soton supports OAI 2.0 with a base URL of http://eprints.soton.ac.uk/cgi/oai2

This repository has been built using EPrints software, developed at the University of Southampton, but available to everyone to use.

We use cookies to ensure that we give you the best experience on our website. If you continue without changing your settings, we will assume that you are happy to receive cookies on the University of Southampton website.

×