Amb motiu del tancament d'estiu, la validació de documents es reprendrà a partir del 28 d'agost de 2026. Disculpeu les molèsties.
Con motivo del cierre de verano, la validación de documentos se reanudará a partir del 28 de agosto de 2026. Disculpad las molestias
Due to the summer closure, document validation will resume starting August 28, 2026. We apologize for any inconvenience.

Asymmetric synthesis of octahydroindoles via a domino robinson annulation/5-endo intramolecular aza-michael reaction

Vista senzilla d'ítem
dc.contributor.authorParra Montes, Claudio
dc.contributor.authorBosch, Caroline
dc.contributor.authorGómez-Bengoa, Enrique
dc.contributor.authorBonjoch i Sesé, Josep
dc.contributor.authorBradshaw, Ben
dc.date.accessioned2017-07-19T15:13:44Z
dc.date.available2017-09-08T22:01:17Z
dc.date.issued2016-09-08
dc.date.updated2017-07-19T15:13:44Z
dc.description.abstractA straightforward two-step asymmetric synthesis of octahydroindoles has been developed based on two complimentary strategies: (i) an organocatalyzed Michael reaction followed by a tandem Robinson-aza-Michael double cyclization catalyzed by PS-BEMP; (ii) a diastereoselective cyclization, which formally constitutes a remote 1,6 asymmetric induction mediated by PS-BEMP. This allowed the construction of complex octahydroindoles with up to 4 stereocenters, excellent enantioselectivities (up to 95% ee) and complete diastereoselective control in a single pot operation. DFT calculations were performed to understand the origin of this effect.
dc.format.extent8 p.
dc.format.mimetypeapplication/pdf
dc.identifier.idgrec666642
dc.identifier.issn0022-3263
dc.identifier.pmid27607430
dc.identifier.urihttps://hdl.handle.net/2445/114102
dc.language.isoeng
dc.publisherAmerican Chemical Society
dc.relation.isformatofVersió postprint del document publicat a: https://doi.org/10.1021/acs.joc.6b01568
dc.relation.ispartofJournal of Organic Chemistry, 2016, vol. 81, p. 10172-10179
dc.relation.urihttps://doi.org/10.1021/acs.joc.6b01568
dc.rights(c) American Chemical Society , 2016
dc.rights.accessRightsinfo:eu-repo/semantics/openAccess
dc.sourceArticles publicats en revistes (Farmacologia, Toxicologia i Química Terapèutica)
dc.subject.classificationQuímica orgànica
dc.subject.classificationSíntesi orgànica
dc.subject.classificationAlcaloides
dc.subject.otherOrganic chemistry
dc.subject.otherOrganic synthesis
dc.subject.otherAlkaloids
dc.titleAsymmetric synthesis of octahydroindoles via a domino robinson annulation/5-endo intramolecular aza-michael reaction
dc.typeinfo:eu-repo/semantics/article
dc.typeinfo:eu-repo/semantics/acceptedVersion

Fitxers

Paquet original

Mostrant 1 - 1 de 1
Miniatura
Nom:
666642.pdf
Mida:
1.08 MB
Format:
Adobe Portable Document Format
Descarregar

Col·leccions

Articles publicats en revistes (Farmacologia, Toxicologia i Química Terapèutica)