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Enhancing the selectivity of prolinamide organocatalysts using the mechanical bond in [2]rotaxanes

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dc.contributor.authorCalles, Maria
dc.contributor.authorPuigcerver, Julio
dc.contributor.authorAlonso, Diego A.
dc.contributor.authorAlajarín, Mateo
dc.contributor.authorMartinez-Cuezva, Alberto
dc.contributor.authorBerná Cánovas, José
dc.contributor.departmentQuímica Orgánica
dc.date.accessioned2021-02-01T18:30:48Z
dc.date.available2021-02-01T18:30:48Z
dc.date.created2020
dc.date.issued2020-03-11
dc.description.abstractThe synthesis of a pair of switchable interlocked prolinamides and their use as organocatalysts in three different enamine-activated processes are reported. A diacylaminopyridine moiety was incorporated into the thread for directing [2]rotaxane formation further allowing the association of complementary small molecules. The rotaxane-based systems were tested as organocatalysts in asymmetric enamine-mediated processes, revealing a significantly improved catalytic ability if compared with the non-interlocked thread. The presence of an electron-withdrawing nitro group at the macrocycle helps to achieve high conversions and enantioselectivities. These systems are able to interact with N-hexylthymine as a cofactor to form supramolecular catalysts displaying a divergent catalytic behaviour. The presence or absence of the cofactor controls the chemoselectivity in competitive reactions.es
dc.formatapplication/pdfes
dc.format.extent7es
dc.identifier.citationChem. Sci., 2020, 11, 3629-3635.
dc.identifier.doi10.1039/D0SC00444H
dc.identifier.issn2041-6520
dc.identifier.issn2041-6539
dc.identifier.urihttp://hdl.handle.net/10201/102322
dc.languageenges
dc.publisherRoyal Society of Chemistryes
dc.relationThis work was supported by the MINECO and MICINN (CTQ2017-87231-P, RYC-2017-22700 and PGC2018-096616-BI00) with joint financing by FEDER Funds and Fundacion Seneca-CARM (Project 20811/PI/18). D. A. A. also thanks the University of Alicante for the financial support (VIGROB-173FI). The authors gratefully acknowledge the computer resources at Cibeles and the technical support provided by the Centro de Computacion Cientifica-UAM (RES-QSB-2019-3-0012).es
dc.relation.isreplacedbyhttps://doi.org/10.1039/D0SC00444Hes
dc.relation.publisherversionhttps://pubs.rsc.org/en/content/articlelanding/2020/sc/d0sc00444hes
dc.rightsinfo:eu-repo/semantics/openAccesses
dc.subjectASYMMETRIC ALDOL REACTIONes
dc.subjectMECHANICAL BONDes
dc.subjectMOLECULAR RECOGNITIONes
dc.subjectMICHAEL ADDITIONSes
dc.subjectROTAXANEes
dc.subjectORGANOCATALYSISes
dc.subject.otherCDU::5 - Ciencias puras y naturales::54 - Química::547 - Química orgánicaes
dc.titleEnhancing the selectivity of prolinamide organocatalysts using the mechanical bond in [2]rotaxaneses
dc.typeinfo:eu-repo/semantics/articlees
dspace.entity.typePublicationes
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