Stereoselective synthesis of indoline, tetrahydroquinoline, and tetrahydrobenzazepine derivatives from o-bromophenyl N-tert-butylsulfinyl aldimines
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Title: | Stereoselective synthesis of indoline, tetrahydroquinoline, and tetrahydrobenzazepine derivatives from o-bromophenyl N-tert-butylsulfinyl aldimines |
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Authors: | Sirvent Pérez, Juan Alberto | Foubelo, Francisco | Yus, Miguel |
Research Group/s: | Síntesis Asimétrica (SINTAS) |
Center, Department or Service: | Universidad de Alicante. Departamento de Química Orgánica | Universidad de Alicante. Instituto Universitario de Síntesis Orgánica |
Keywords: | Chiral sulfinyl imines | Diastereoselective addition | Intramolecular N-arylation | Indolizidine | Quinolizidine | Indoline | Tetrahydroquinoline | Benzazepine | (-)-angustureine |
Knowledge Area: | Química Orgánica |
Issue Date: | 21-Jan-2014 |
Publisher: | American Chemical Society |
Citation: | Journal of Organic Chemistry. 2014, 79(3): 1356-1367. doi:10.1021/jo402759v |
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). |
Sponsor: | 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. |
URI: | http://hdl.handle.net/10045/35519 |
ISSN: | 0022-3263 (Print) | 1520-6904 (Online) |
DOI: | 10.1021/jo402759v |
Language: | eng |
Type: | info:eu-repo/semantics/article |
Rights: | Copyright © 2014 American Chemical Society |
Peer Review: | si |
Publisher version: | http://dx.doi.org/10.1021/jo402759v |
Appears in Collections: | INV - SINTAS - Artículos de Revistas |
Files in This Item:
File | Description | Size | Format | |
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2014_Sirvent_etal_JOC.pdf | Versión revisada (acceso abierto) | 746,84 kB | Adobe PDF | Open Preview |
2014_Sirvent_etal_JOC-final.pdf | Versión final (acceso restringido) | 1,13 MB | Adobe PDF | Open Request a copy |
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