Organocatalyzed Michael addition reaction by novel (2R,3aS,7aS)-octa-hydroindole-2-carboxylic acid, a new fused proline

We present here the results obtained in our study on organocatalytic enantioselective Michael addition reaction of acetone to different nitroolefines using (2R,3aS,7aS)-octahydroindole-2-carboxylic acid [(R,S,S)-Oic] as a new and suitable catalyst for this process. Computational calculations support...

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Detalles Bibliográficos
Autores: Roca-López, David, Merino, Pedro, Sayago, Francisco J., Cativiela, Carlos, Herrera, Raquel P.
Tipo de recurso: artículo
Estado:Versión aceptada para publicación
Fecha de publicación:2011
País:España
Institución:Consejo Superior de Investigaciones Científicas (CSIC)
Repositorio:DIGITAL.CSIC. Repositorio Institucional del CSIC
OAI Identifier:oai:digital.csic.es:10261/113976
Acceso en línea:http://hdl.handle.net/10261/113976
Access Level:acceso abierto
Palabra clave:Ketones
Nitroolefines
Oic
Organocatalysis
Enantioselectivity
Michael addition
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spelling Organocatalyzed Michael addition reaction by novel (2R,3aS,7aS)-octa-hydroindole-2-carboxylic acid, a new fused prolineRoca-López, DavidMerino, PedroSayago, Francisco J.Cativiela, CarlosHerrera, Raquel P.KetonesNitroolefinesOicOrganocatalysisEnantioselectivityMichael additionWe present here the results obtained in our study on organocatalytic enantioselective Michael addition reaction of acetone to different nitroolefines using (2R,3aS,7aS)-octahydroindole-2-carboxylic acid [(R,S,S)-Oic] as a new and suitable catalyst for this process. Computational calculations support the results obtained with (R,S,S)-Oic versus its diastereomeric form (S,S,S)-Oic. The final products are obtained in good yields and moderate enantioselectivities (up to 58% ee). © Georg Thieme Verlag Stuttgart.We thank the Spanish National Research Council (CSIC. Project PIE-200880I260), the Ministry of Science and Innovation (MICINN, Madrid; Projects CTQ2009-09028, CTQ2010-19606, and CTQ2010-17436) and the Government of Aragón (Zaragoza; Project PI064/09 and Research Groups E-10 and E-40) for financial support of our research. R.P.H. thanks the Aragón I + D Foundation for her permanent contract.Peer ReviewedThiemeGobierno de AragónFundación Agencia Aragonesa para la Investigación y el DesarrolloMinisterio de Ciencia e Innovación (España)Consejo Superior de Investigaciones Científicas (España)Consejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]2015201520112015info:eu-repo/semantics/articlehttp://purl.org/coar/resource_type/c_6501Postprintinfo:eu-repo/semantics/acceptedVersionhttp://hdl.handle.net/10261/113976reponame:DIGITAL.CSIC. Repositorio Institucional del CSICinstname:Consejo Superior de Investigaciones Científicas (CSIC)Ingléshttp://dx.doi.org/10.1055/s-0030-1259296Síinfo:eu-repo/semantics/openAccessoai:digital.csic.es:10261/1139762026-05-22T06:33:51Z
dc.title.none.fl_str_mv Organocatalyzed Michael addition reaction by novel (2R,3aS,7aS)-octa-hydroindole-2-carboxylic acid, a new fused proline
title Organocatalyzed Michael addition reaction by novel (2R,3aS,7aS)-octa-hydroindole-2-carboxylic acid, a new fused proline
spellingShingle Organocatalyzed Michael addition reaction by novel (2R,3aS,7aS)-octa-hydroindole-2-carboxylic acid, a new fused proline
Roca-López, David
Ketones
Nitroolefines
Oic
Organocatalysis
Enantioselectivity
Michael addition
title_short Organocatalyzed Michael addition reaction by novel (2R,3aS,7aS)-octa-hydroindole-2-carboxylic acid, a new fused proline
title_full Organocatalyzed Michael addition reaction by novel (2R,3aS,7aS)-octa-hydroindole-2-carboxylic acid, a new fused proline
title_fullStr Organocatalyzed Michael addition reaction by novel (2R,3aS,7aS)-octa-hydroindole-2-carboxylic acid, a new fused proline
title_full_unstemmed Organocatalyzed Michael addition reaction by novel (2R,3aS,7aS)-octa-hydroindole-2-carboxylic acid, a new fused proline
title_sort Organocatalyzed Michael addition reaction by novel (2R,3aS,7aS)-octa-hydroindole-2-carboxylic acid, a new fused proline
dc.creator.none.fl_str_mv Roca-López, David
Merino, Pedro
Sayago, Francisco J.
Cativiela, Carlos
Herrera, Raquel P.
author Roca-López, David
author_facet Roca-López, David
Merino, Pedro
Sayago, Francisco J.
Cativiela, Carlos
Herrera, Raquel P.
author_role author
author2 Merino, Pedro
Sayago, Francisco J.
Cativiela, Carlos
Herrera, Raquel P.
author2_role author
author
author
author
dc.contributor.none.fl_str_mv Gobierno de Aragón
Fundación Agencia Aragonesa para la Investigación y el Desarrollo
Ministerio de Ciencia e Innovación (España)
Consejo Superior de Investigaciones Científicas (España)
Consejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]
dc.subject.none.fl_str_mv Ketones
Nitroolefines
Oic
Organocatalysis
Enantioselectivity
Michael addition
topic Ketones
Nitroolefines
Oic
Organocatalysis
Enantioselectivity
Michael addition
description We present here the results obtained in our study on organocatalytic enantioselective Michael addition reaction of acetone to different nitroolefines using (2R,3aS,7aS)-octahydroindole-2-carboxylic acid [(R,S,S)-Oic] as a new and suitable catalyst for this process. Computational calculations support the results obtained with (R,S,S)-Oic versus its diastereomeric form (S,S,S)-Oic. The final products are obtained in good yields and moderate enantioselectivities (up to 58% ee). © Georg Thieme Verlag Stuttgart.
publishDate 2011
dc.date.none.fl_str_mv 2011
2015
2015
2015
dc.type.none.fl_str_mv info:eu-repo/semantics/article
http://purl.org/coar/resource_type/c_6501
Postprint
info:eu-repo/semantics/acceptedVersion
format article
status_str acceptedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/10261/113976
url http://hdl.handle.net/10261/113976
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv http://dx.doi.org/10.1055/s-0030-1259296
Sí
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.publisher.none.fl_str_mv Thieme
publisher.none.fl_str_mv Thieme
dc.source.none.fl_str_mv reponame:DIGITAL.CSIC. Repositorio Institucional del CSIC
instname:Consejo Superior de Investigaciones Científicas (CSIC)
instname_str Consejo Superior de Investigaciones Científicas (CSIC)
reponame_str DIGITAL.CSIC. Repositorio Institucional del CSIC
collection DIGITAL.CSIC. Repositorio Institucional del CSIC
repository.name.fl_str_mv
repository.mail.fl_str_mv
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score 15,812429

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