Stereoselective synthesis of indoline, tetrahydroquinoline, and tetrahydrobenzazepine derivatives from o-bromophenyl N-tert-butylsulfinyl aldimines

Please use this identifier to cite or link to this item: http://hdl.handle.net/10045/35519
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dc.contributorSíntesis Asimétrica (SINTAS)es
dc.contributor.authorSirvent Pérez, Juan Alberto-
dc.contributor.authorFoubelo, Francisco-
dc.contributor.authorYus, Miguel-
dc.contributor.otherUniversidad de Alicante. Departamento de Química Orgánicaes
dc.contributor.otherUniversidad de Alicante. Instituto Universitario de Síntesis Orgánicaes
dc.date.accessioned2014-02-13T09:49:29Z-
dc.date.available2014-02-13T09:49:29Z-
dc.date.issued2014-01-21-
dc.identifier.citationJournal of Organic Chemistry. 2014, 79(3): 1356-1367. doi:10.1021/jo402759ves
dc.identifier.issn0022-3263 (Print)-
dc.identifier.issn1520-6904 (Online)-
dc.identifier.urihttp://hdl.handle.net/10045/35519-
dc.description.abstractThe diastereoselective addition of an allylic indium intermediate to chiral o-bromophenyl sulfinyl imine 4 proceeded with good levels of diastereoselectivity. The resulting homoallylic amine derivatives were transformed into lactams 7 and 12, which upon copper-mediated intramolecular N-arylation led to the formation of benzo-fused 1-azabicyclo[j.k.0]alkanes 8 and 13. Benzo-fused 2-allyl-substituted heterocycles 14 could also be prepared by means of a palladium-catalyzed N-arylation of the corresponding free amines. The synthesis of the alkaloid (−)-angustureine was easily accomplished from (S)-2-allyltetrahydroquinoline (14b).es
dc.description.sponsorshipSpanish Ministerio de Ciencia e Innovación (Grants CTQ2007-65218, Consolider Ingenio 2010-CSD-2007-00006, and CTQ2011-24165), the Generalitat Valenciana (Grant PROMETEO/2009/039 and FEDER), and the University of Alicante.es
dc.languageenges
dc.publisherAmerican Chemical Societyes
dc.rightsCopyright © 2014 American Chemical Societyes
dc.subjectChiral sulfinyl imineses
dc.subjectDiastereoselective additiones
dc.subjectIntramolecular N-arylationes
dc.subjectIndolizidinees
dc.subjectQuinolizidinees
dc.subjectIndolinees
dc.subjectTetrahydroquinolinees
dc.subjectBenzazepinees
dc.subject(-)-angustureinees
dc.subject.otherQuímica Orgánicaes
dc.titleStereoselective synthesis of indoline, tetrahydroquinoline, and tetrahydrobenzazepine derivatives from o-bromophenyl N-tert-butylsulfinyl aldimineses
dc.typeinfo:eu-repo/semantics/articlees
dc.peerreviewedsies
dc.identifier.doi10.1021/jo402759v-
dc.relation.publisherversionhttp://dx.doi.org/10.1021/jo402759ves
dc.rights.accessRightsinfo:eu-repo/semantics/openAccesses
Appears in Collections:INV - SINTAS - Artículos de Revistas

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