A co-conformationally "topologically" chiral catenane

Arnau Rodríguez-Rubio; Andrea Savoini; Florian Modicom; Patrick Butler; Stephen M. Goldup

doi:10.1021/jacs.2c02029

A co-conformationally "topologically" chiral catenane

Arnau Rodríguez-Rubio, Andrea Savoini, Florian Modicom, Patrick Butler, Stephen M. Goldup^*

^*Corresponding author for this work

Chemistry

Research output: Contribution to journal › Article › peer-review

2 Citations (Scopus)

39 Downloads (Pure)

Abstract

Catenanes composed of two achiral rings that are oriented (C_nhsymmetry) because of the sequence of atoms they contain are referred to as topologically chiral. Here, we present the synthesis of a highly enantioenriched catenane containing a related but overlooked "co-conformationally ‘topologically' chiral" stereogenic unit, which arises when a bilaterally symmetric C_nvring is desymmetrized by the position of an oriented macrocycle.

Original language	English
Pages (from-to)	11927-11932
Number of pages	6
Journal	Journal of the American Chemical Society
Volume	144
Issue number	27
Early online date	28 Jun 2022
DOIs	https://doi.org/10.1021/jacs.2c02029
Publication status	Published - 13 Jul 2022

Bibliographical note

Funding Information:
S.M.G. thanks the ERC (Agreement No. 724987) for funding and the Royal Society for a Wolfson Research Fellowship (RSWF\FT\180010). P.B. thanks the University of Southampton for a Presidential Scholarship. F.M. thanks the ESPRC for a Doctoral Prize Scholarship (EP/R513325/1).

Publisher Copyright:
© 2022 American Chemical Society. All rights reserved.

ASJC Scopus subject areas

Catalysis
General Chemistry
Biochemistry
Colloid and Surface Chemistry

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10.1021/jacs.2c02029Licence: Creative Commons: Attribution (CC BY)

RodríguezRubioA2022CoconformationallyFinal published version, 1.92 MBLicence: Creative Commons: Attribution (CC BY)

Cite this

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AU - Rodríguez-Rubio, Arnau

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AU - Modicom, Florian

AU - Butler, Patrick

AU - Goldup, Stephen M.

N1 - Funding Information: S.M.G. thanks the ERC (Agreement No. 724987) for funding and the Royal Society for a Wolfson Research Fellowship (RSWF\FT\180010). P.B. thanks the University of Southampton for a Presidential Scholarship. F.M. thanks the ESPRC for a Doctoral Prize Scholarship (EP/R513325/1). Publisher Copyright: © 2022 American Chemical Society. All rights reserved.

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N2 - Catenanes composed of two achiral rings that are oriented (Cnhsymmetry) because of the sequence of atoms they contain are referred to as topologically chiral. Here, we present the synthesis of a highly enantioenriched catenane containing a related but overlooked "co-conformationally ‘topologically' chiral" stereogenic unit, which arises when a bilaterally symmetric Cnvring is desymmetrized by the position of an oriented macrocycle.

AB - Catenanes composed of two achiral rings that are oriented (Cnhsymmetry) because of the sequence of atoms they contain are referred to as topologically chiral. Here, we present the synthesis of a highly enantioenriched catenane containing a related but overlooked "co-conformationally ‘topologically' chiral" stereogenic unit, which arises when a bilaterally symmetric Cnvring is desymmetrized by the position of an oriented macrocycle.

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A co-conformationally "topologically" chiral catenane

Abstract

Bibliographical note

ASJC Scopus subject areas

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