Publication: Mechanically Planar-to-Point Chirality Transmission in [2]Rotaxanes
Loading...
Date
2024-01-24
Authors
Puigcerver, Julio ; Marin-Luna, Marta ; Iglesias-Sigüenza, Javier ; Alajarin, Mateo ; Martinez-Cuezva, Alberto ; Berna, Jose
item.page.secondaryauthor
item.page.director
Publisher
American Chemical Society
publication.page.editor
publication.page.department
DOI
https://doi.org/10.1021/jacs.3c11611
item.page.type
info:eu-repo/semantics/article
Description
© 2024. The authors. This document is made available under the CC-BY 4.0 license http://creativecommons.org/licenses/by /4.0/
This document is the published version of a published work that appeared in final form in Journal of the American Chemical Society (JACS).
To access the final work, see DOI: https://doi.org/10.1021/jacs.3c11611
Abstract
Herein we describe an effective transmission of chirality, from mechanically planar chirality to point chirality, in
hydrogen-bonded [2]rotaxanes. A highly selective mono-N-methylation of one (out of four) amide N atom at the macrocyclic
counterpart of starting achiral rotaxanes generates mechanically planar chirality. Followed by chiral resolution, both enantiomers
were subjected to a base-promoted intramolecular cyclization, where their interlocked threads were transformed into new lactam
moieties. As a matter of fact, the mechanically planar chiral information was effectively transferred to the resulting stereocenters
(covalent chirality) of the newly formed heterocycles. Upon removing the entwined macrocycle, the final lactams were obtained with
high enantiopurity.
publication.page.subject
Citation
Journal of the American Chemical Society (JACS) 2024, 146, pp.2882−2887
item.page.embargo
Collections
Ir a Estadísticas
Este ítem está sujeto a una licencia Creative Commons. http://creativecommons.org/licenses/by/4.0/