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

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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

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