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Role of association in chiral catalysis: from asymmetric synthesis to spin selectivity

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Role of association in chiral catalysis: from asymmetric synthesis to spin selectivity

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dc.contributor.author Ageeva, A.A. es_ES
dc.contributor.author Khramtsova, E.A. es_ES
dc.contributor.author Magin, I.M. es_ES
dc.contributor.author Purtov, P.A. es_ES
dc.contributor.author Miranda Alonso, Miguel Ángel es_ES
dc.contributor.author Leshina, T.V. es_ES
dc.date.accessioned 2020-07-11T03:31:05Z
dc.date.available 2020-07-11T03:31:05Z
dc.date.issued 2018-12-12 es_ES
dc.identifier.issn 0947-6539 es_ES
dc.identifier.uri http://hdl.handle.net/10251/147777
dc.description "This is the peer reviewed version of the following article: Ageeva, Aleksandra A., Ekaterina A. Khramtsova, Ilya M. Magin, Peter A. Purtov, Miguel A. Miranda, and Tatyana V. Leshina. 2018. Role of Association in Chiral Catalysis: From Asymmetric Synthesis to Spin Selectivity. Chemistry A European Journal 24 (70). Wiley: 18587 600. doi:10.1002/chem.201801625, which has been published in final form at https://doi.org/10.1002/chem.201801625. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Self-Archiving." es_ES
dc.description.abstract [EN] The origin of biomolecules in the pre-biological period is still a matter of debate, as is the unclarified nature of the differences in enantiomer properties, especially for the medically important activity of chiral drugs. With regards to the first issue, significant progress was made in the last decade of the 20th century through experimental confirmation of Frank's popular theory on chiral catalysis in spontaneous asymmetric synthesis. Soai examined the chiral catalysis of the alkylation of achiral aldehydes by achiral reagents. Attempts to model this process demonstrated the key role of chiral compounds associates as templates for chiral synthesis. However, the elementary mechanism of alkylation and the role of free radicals in this process are still incompletely understood. Meanwhile, the influence of external magnetic fields on chiral enrichment in the radical path of alkylation has been predicted. In addition, the role of chiral dyad association in another radical process, electron transfer (ET), has been recently demonstrated by the following methods: chemically induced dynamic nuclear polarisation (CIDNP), NMR spectroscopy, XRD and photochemistry. The CIDNP analysis of ET in two dyads has revealed a phenomenon first observed for chiral systems, spin selectivity, which results in the difference between the CIDNP enhancement coefficients of dyad diastereomers. These dyads are linked systems consisting of the widespread drug (S)-naproxen (NPX) or its R analogue and electron donors, namely, (S)-tryptophan and (S)-N-methylpyrrolidine. Because NPX is one of the most striking examples of the difference in the therapeutic properties of enantiomers, the appearance of spin selectivity in dyads with (S)- and (R)-NPX and S donors can shed light on the chemical nature of these differences. This review is devoted to discussing the chemical nature of spin selectivity and the role of chiral associates in the chiral catalysis of an elementary radical reaction: ET in chiral dyads. es_ES
dc.description.sponsorship The work was supported by the Russian Science Foundation (18-13-00047). es_ES
dc.language Inglés es_ES
dc.publisher John Wiley & Sons es_ES
dc.relation.ispartof Chemistry - A European Journal es_ES
dc.rights Reserva de todos los derechos es_ES
dc.subject Asymmetric catalysis es_ES
dc.subject Chirality es_ES
dc.subject Electron transfer es_ES
dc.subject Enantioselectivity es_ES
dc.subject Spin selectivity es_ES
dc.subject.classification QUIMICA ORGANICA es_ES
dc.title Role of association in chiral catalysis: from asymmetric synthesis to spin selectivity es_ES
dc.type Artículo es_ES
dc.identifier.doi 10.1002/chem.201801625 es_ES
dc.relation.projectID info:eu-repo/grantAgreement/RFBR//8-13-00047/ es_ES
dc.rights.accessRights Abierto es_ES
dc.contributor.affiliation Universitat Politècnica de València. Departamento de Química - Departament de Química es_ES
dc.description.bibliographicCitation Ageeva, A.; Khramtsova, E.; Magin, I.; Purtov, P.; Miranda Alonso, MÁ.; Leshina, T. (2018). Role of association in chiral catalysis: from asymmetric synthesis to spin selectivity. Chemistry - A European Journal. 24(70):18587-18600. https://doi.org/10.1002/chem.201801625 es_ES
dc.description.accrualMethod S es_ES
dc.relation.publisherversion https://doi.org/10.1002/chem.201801625 es_ES
dc.description.upvformatpinicio 18587 es_ES
dc.description.upvformatpfin 18600 es_ES
dc.type.version info:eu-repo/semantics/publishedVersion es_ES
dc.description.volume 24 es_ES
dc.description.issue 70 es_ES
dc.identifier.pmid 29932476 es_ES
dc.relation.pasarela S\388446 es_ES
dc.contributor.funder Russian Science Foundation es_ES
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