Publication:
Mechanically Planar-to-Point Chirality Transmission in [2]Rotaxanes

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dc.contributor.authorPuigcerver, Julio
dc.contributor.authorMarin-Luna, Marta
dc.contributor.authorIglesias-Sigüenza, Javier
dc.contributor.authorAlajarin, Mateo
dc.contributor.authorMartinez-Cuezva, Alberto
dc.contributor.authorBerna, Jose
dc.contributor.departmentQuímica Orgánica
dc.date.accessioned2024-03-05T12:33:09Z
dc.date.available2024-03-05T12:33:09Z
dc.date.issued2024-01-24
dc.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.3c11611es
dc.description.abstractHerein 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.es
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dc.format.extent6es
dc.identifier.citationJournal of the American Chemical Society (JACS) 2024, 146, pp.2882−2887
dc.identifier.doihttps://doi.org/10.1021/jacs.3c11611
dc.identifier.urihttp://hdl.handle.net/10201/139945
dc.languageenges
dc.publisherAmerican Chemical Societyes
dc.relationThis research was supported by the Spanish Ministry of Science and Innovation (Grants PID2019-106358GB-C22 and PID2020-113686GB-I00/MCIN/AEI/10.13039/501100- 011033) and Fundacion Seneca-CARM (Project 21907/PI/22). J.P. also thanks the MICINN for his predoctoral contract (FPU19/05419).es
dc.relation.publisherversionhttps://pubs.acs.org/doi/10.1021/jacs.3c11611es
dc.relation.requireshttp://hdl.handle.net/10201/139889es
dc.rightsinfo:eu-repo/semantics/openAccesses
dc.rightsAtribución 4.0 Internacional*
dc.rights.urihttp://creativecommons.org/licenses/by/4.0/*
dc.titleMechanically Planar-to-Point Chirality Transmission in [2]Rotaxaneses
dc.typeinfo:eu-repo/semantics/articlees
dspace.entity.typePublicationes
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