Stereoselective synthesis of indoline, tetrahydroquinoline, and tetrahydrobenzazepine derivatives from o-bromophenyl N-tert-butylsulfinyl aldimines
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http://hdl.handle.net/10045/35519
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Camp Dublin Core | Valor | Idioma |
---|---|---|
dc.contributor | Síntesis Asimétrica (SINTAS) | es |
dc.contributor.author | Sirvent Pérez, Juan Alberto | - |
dc.contributor.author | Foubelo, Francisco | - |
dc.contributor.author | Yus, Miguel | - |
dc.contributor.other | Universidad de Alicante. Departamento de Química Orgánica | es |
dc.contributor.other | Universidad de Alicante. Instituto Universitario de Síntesis Orgánica | es |
dc.date.accessioned | 2014-02-13T09:49:29Z | - |
dc.date.available | 2014-02-13T09:49:29Z | - |
dc.date.issued | 2014-01-21 | - |
dc.identifier.citation | Journal of Organic Chemistry. 2014, 79(3): 1356-1367. doi:10.1021/jo402759v | es |
dc.identifier.issn | 0022-3263 (Print) | - |
dc.identifier.issn | 1520-6904 (Online) | - |
dc.identifier.uri | http://hdl.handle.net/10045/35519 | - |
dc.description.abstract | The 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.sponsorship | Spanish 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.language | eng | es |
dc.publisher | American Chemical Society | es |
dc.rights | Copyright © 2014 American Chemical Society | es |
dc.subject | Chiral sulfinyl imines | es |
dc.subject | Diastereoselective addition | es |
dc.subject | Intramolecular N-arylation | es |
dc.subject | Indolizidine | es |
dc.subject | Quinolizidine | es |
dc.subject | Indoline | es |
dc.subject | Tetrahydroquinoline | es |
dc.subject | Benzazepine | es |
dc.subject | (-)-angustureine | es |
dc.subject.other | Química Orgánica | es |
dc.title | Stereoselective synthesis of indoline, tetrahydroquinoline, and tetrahydrobenzazepine derivatives from o-bromophenyl N-tert-butylsulfinyl aldimines | es |
dc.type | info:eu-repo/semantics/article | es |
dc.peerreviewed | si | es |
dc.identifier.doi | 10.1021/jo402759v | - |
dc.relation.publisherversion | http://dx.doi.org/10.1021/jo402759v | es |
dc.rights.accessRights | info:eu-repo/semantics/openAccess | es |
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2014_Sirvent_etal_JOC.pdf | Versión revisada (acceso abierto) | 746,84 kB | Adobe PDF | Obrir Vista prèvia |
2014_Sirvent_etal_JOC-final.pdf | Versión final (acceso restringido) | 1,13 MB | Adobe PDF | Obrir Sol·licitar una còpia |
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