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An auxiliary approach for the stereoselective synthesis of topologically chiral catenanes

An auxiliary approach for the stereoselective synthesis of topologically chiral catenanes
An auxiliary approach for the stereoselective synthesis of topologically chiral catenanes
Catenanes, molecules in which two rings are threaded through one another like links in a chain, can form as two structures related as object and mirror image but otherwise identical if the individual rings lack bilateral symmetry. These structures are described as “topologically chiral” as, unlike most chiral molecules, it is not possible to convert one mirror-image form to the other under the rules of mathematical topology. Although intriguing, and discussed as early as 1961, to date all methods to access molecules containing only this topological stereogenic element require the separation of the mirror image forms using chiral stationary phase high performance liquid chromatography (PCSP-HPLC) which has limited their investigation to date. Here we present a simple method that uses a readily available source of chiral information to allow the stereoselective synthesis of topologically chiral catenanes.
2451-9308
1512-1520
Goldup, Stephen. M
0a93eedd-98bb-42c1-a963-e2815665e937
Denis, Mathieu
05f9a9b4-df98-4cc8-bebf-33e99bc91e7d
Modicom, Florian
55fa7615-b786-41d2-9a00-c617a774f2cf
Lewis, James.E.M.
424e2715-a4ee-46b0-b7bf-df6fb0f04779
Goldup, Stephen. M
0a93eedd-98bb-42c1-a963-e2815665e937
Denis, Mathieu
05f9a9b4-df98-4cc8-bebf-33e99bc91e7d
Modicom, Florian
55fa7615-b786-41d2-9a00-c617a774f2cf
Lewis, James.E.M.
424e2715-a4ee-46b0-b7bf-df6fb0f04779

Goldup, Stephen. M, Denis, Mathieu, Modicom, Florian and Lewis, James.E.M. (2019) An auxiliary approach for the stereoselective synthesis of topologically chiral catenanes. Chem, 5 (6), 1512-1520. (doi:10.1016/j.chempr.2019.03.008).

Record type: Article

Abstract

Catenanes, molecules in which two rings are threaded through one another like links in a chain, can form as two structures related as object and mirror image but otherwise identical if the individual rings lack bilateral symmetry. These structures are described as “topologically chiral” as, unlike most chiral molecules, it is not possible to convert one mirror-image form to the other under the rules of mathematical topology. Although intriguing, and discussed as early as 1961, to date all methods to access molecules containing only this topological stereogenic element require the separation of the mirror image forms using chiral stationary phase high performance liquid chromatography (PCSP-HPLC) which has limited their investigation to date. Here we present a simple method that uses a readily available source of chiral information to allow the stereoselective synthesis of topologically chiral catenanes.

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More information

Accepted/In Press date: 28 February 2019
e-pub ahead of print date: 11 April 2019
Published date: 13 June 2019

Identifiers

Local EPrints ID: 428628
URI: http://eprints.soton.ac.uk/id/eprint/428628
ISSN: 2451-9308
PURE UUID: b79aec51-0291-4884-8d4b-c77304b88ca3
ORCID for Stephen. M Goldup: ORCID iD orcid.org/0000-0003-3781-0464

Catalogue record

Date deposited: 05 Mar 2019 17:30
Last modified: 15 Sep 2021 04:10

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