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Please use this identifier to cite or link to this item: http://hdl.handle.net/2445/114102
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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.identifier.issn0022-3263-
dc.identifier.urihttp://hdl.handle.net/2445/114102-
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.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.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-
dc.identifier.idgrec666642-
dc.date.updated2017-07-19T15:13:44Z-
dc.rights.accessRightsinfo:eu-repo/semantics/openAccess-
dc.identifier.pmid27607430-
Appears in Collections:Articles publicats en revistes (Farmacologia, Toxicologia i Química Terapèutica)

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