Heterocycle-based bifunctional organocatalysts in asymmetric synthesis
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Campo DC | Valor | Idioma |
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dc.contributor | Síntesis Asimétrica (SINTAS) | es_ES |
dc.contributor.author | Nájera, Carmen | - |
dc.contributor.author | Sansano, Jose M. | - |
dc.contributor.author | Gómez Bengoa, Enrique | - |
dc.contributor.other | Universidad de Alicante. Departamento de Química Orgánica | es_ES |
dc.date.accessioned | 2016-11-03T13:44:35Z | - |
dc.date.available | 2016-11-03T13:44:35Z | - |
dc.date.issued | 2016-07-28 | - |
dc.identifier.citation | Pure and Applied Chemistry. 2016, 88(6): 561-578. doi:10.1515/pac-2016-0403 | es_ES |
dc.identifier.issn | 0033-4545 (Print) | - |
dc.identifier.issn | 1365-3075 (Online) | - |
dc.identifier.uri | http://hdl.handle.net/10045/59654 | - |
dc.description.abstract | Different chiral bifunctional organocatalysts derived from trans-cyclohexane-1,2-diamine bearing different types of guanidine units able to form-hydrogen bonding activation have been designed. Conformational rigid 2-aminobenzimidazoles bearing a tertiary amino group have been used in enantioselective Michael type reactions of activated methylene compounds to nitroalkenes. The C2 symmetric bis(2-aminobenzimidazole) derivatives the appropriate organocatalyst for the conjugate addition of 1,3-dicarbonyl compounds to maleimides as well as for the SN1 reaction of benzylic alcohols with carbon nucleophiles. 2-Aminobenzimidazoles bearing a primary amino group have shown excellent catalytic activity in the Michael reaction of aldehydes to maleimides and nitroalkenes. Diastereomeric 2-aminopyrimidines bearing a prolinamide unit have been incorporated in the trans-cyclohexane-1,2-diamine scaffold and have been used for the inter- and intra-molecular direct aldol reaction under solvent-free conditions. For the Michael reaction of aldehydes with maleimides the primary amine 2-aminopyrimidine has shown excellent efficiency as organocatalyst. The bifunctional character of these organocatalysts has been demonstrated by means of DFT calculations. | es_ES |
dc.description.sponsorship | The Spanish Ministerio de Ciencia e Innovación (MICINN) (projects CTQ2010-20387, and Consolider Ingenio 2010, CSD2007-00006), the Spanish Ministerio de Economía y Competitividad (MINECO) (projects CTQ2013-43446-P and CTQ2014-51912-REDC), FEDER, the Generalitat Valenciana (PROMETEO 2009/039 and PROMETEOII/2014/017), the Basque Government (GV Grant IT-291-07), the FP7 Marie Curie Actions of the European Commission via the ITN ECHONET network (MCITN-2012-316379) and the Universities of Alicante and Basque Country are gratefully acknowledged for financial support. We also thank for technical and human support provided by IZO-SGI SGIker of UPV-EHU and European funding (ERDF and ESF). | es_ES |
dc.language | eng | es_ES |
dc.publisher | De Gruyter | es_ES |
dc.rights | © 2016 IUPAC & De Gruyter. This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License. For more information, please visit: http://creativecommons.org/licenses/by-nc-nd/4.0/ | es_ES |
dc.subject | Aldols | es_ES |
dc.subject | Asymmetric synthesis | es_ES |
dc.subject | Bifunctional catalysis | es_ES |
dc.subject | Carbenium ions | es_ES |
dc.subject | 1,3-dicarbonyl compounds | es_ES |
dc.subject | Hydrogen bonding | es_ES |
dc.subject | Nitro compounds | es_ES |
dc.subject | Succinimides | es_ES |
dc.subject | TRAMECH VIII | es_ES |
dc.subject.other | Química Orgánica | es_ES |
dc.title | Heterocycle-based bifunctional organocatalysts in asymmetric synthesis | es_ES |
dc.type | info:eu-repo/semantics/article | es_ES |
dc.peerreviewed | si | es_ES |
dc.identifier.doi | 10.1515/pac-2016-0403 | - |
dc.relation.publisherversion | http://dx.doi.org/10.1515/pac-2016-0403 | es_ES |
dc.rights.accessRights | info:eu-repo/semantics/openAccess | es_ES |
dc.relation.projectID | info:eu-repo/grantAgreement/EC/FP7/316379 | es_ES |
Aparece en las colecciones: | INV - SINTAS - Artículos de Revistas Investigaciones financiadas por la UE |
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