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Ring-to-thread chirality transfer in [2]rotaxanes for the synthesis of enantioenriched lactams

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dc.contributor.advisorMartinez-Cuezva, Alberto
dc.contributor.advisorBerna, José
dc.contributor.authorLopez-Leonardo, Carmen
dc.contributor.authorSaura Sanmartín, Adrián
dc.contributor.authorMarin-Luna, Marta
dc.contributor.authorAlajarín, Mateo
dc.contributor.authorMartinez-Cuezva, Alberto
dc.contributor.authorBerna, Jose
dc.contributor.departmentQuímica Orgánica
dc.date.accessioned2023-11-16T07:43:18Z
dc.date.available2023-11-16T07:43:18Z
dc.date.issued2022-09-19
dc.description© 2022, The Authors. This manuscript version is made available under the CC-BY-NC 4.0 license https://creativecommons.org/licenses/by-nc/4.0/ This document is the Published version of a Published Work that appeared in final form in Angewandte Chemie International Edition. To access the final edited and published work see https://doi.org/10.1002/anie.202209904es
dc.description.abstractThe synthesis of chiral mechanically interlocked molecules has attracted a lot of attention in the last few years, with applications in different fields, such as asymmetric catalysis or sensing. Herein we describe the synthesis of orientational mechanostereoisomers, which include a benzylic amide macrocycle with a stereogenic center, and nonsymmetric N-(arylmethyl)fumaramides as the axis. The base-promoted cyclization of the initial fumaramide thread allows enantioenriched value-added compounds, such as lactams of different ring sizes and amino acids, to be obtained. The chiral information is effectively transmitted across the mechanical bond from the encircling ring to the interlocked lactam. High levels of enantioselectivity and full control of the regioselectivity of the final cyclic compounds are attained.es
dc.formatapplication/pdfes
dc.format.extent10es
dc.identifier.citationAngewandte Chemie International Edition, 61, 39, 2022, e202209904
dc.identifier.doihttps://doi.org/10.1002/anie.202209904
dc.identifier.issnPrint: 1433-7851
dc.identifier.issnElectronic: 1521-3773
dc.identifier.urihttp://hdl.handle.net/10201/135763
dc.languageenges
dc.publisherWiley-VCHes
dc.relationMICIN/AEI/10.13039/501100011033 (Project PID2020-113686GBI00); Fundacion Seneca-CARM (Project 20811/PI/18 and contract 20259/FPI/17); European Union—NextGenerationEU (Margarita Salas postdoctoral contract, Ministerio de Universidades of the Government of Spain).es
dc.relation.publisherversionhttps://onlinelibrary.wiley.com/doi/10.1002/anie.202209904
dc.rightsinfo:eu-repo/semantics/openAccesses
dc.rightsAtribución-NoComercial 4.0 Internacional*
dc.rights.urihttp://creativecommons.org/licenses/by-nc/4.0/*
dc.subjectBase-Promoted Cyclizationes
dc.subjectChirality Transfer Processes
dc.subjectEnantioselectivees
dc.subjectHydrogen-Bonded Rotaxaneses
dc.subjectMechanostereoisomerses
dc.subject.otherCDU::5 - Ciencias puras y naturales::54 - Química::547 - Química orgánicaes
dc.titleRing-to-thread chirality transfer in [2]rotaxanes for the synthesis of enantioenriched lactamses
dc.typeinfo:eu-repo/semantics/articlees
dspace.entity.typePublicationes
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