Natural amino acids as chiral auxiliaries in asymmetric Diels-Alder reactions

To test whether a-amino acids can be efficient chiral auxiliaries in asymmetric Diels-Alder reactions, the chiral dienophile N-acryloyl-L-phenylalanine methyl ester was made to react with cyclopentadiene. Diastereofacial selectivity is to a great extent dependent on the Lewis acid used to promote th...

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Autores: Bueno, María P., Cativiela, Carlos, Mayoral, José A., Avenoza, Alberto, Charro, Paula, Roy, Miguel A., Andrés Gimeno, José Manuel
Tipo de recurso: artículo
Estado:Versión aceptada para publicación
Fecha de publicación:1988
País:España
Institución:Consejo Superior de Investigaciones Científicas (CSIC)
Repositorio:DIGITAL.CSIC. Repositorio Institucional del CSIC
OAI Identifier:oai:digital.csic.es:10261/167788
Acceso en línea:http://hdl.handle.net/10261/167788
Access Level:acceso abierto
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spelling Natural amino acids as chiral auxiliaries in asymmetric Diels-Alder reactionsBueno, María P.Cativiela, CarlosMayoral, José A.Avenoza, AlbertoCharro, PaulaRoy, Miguel A.Andrés Gimeno, José ManuelTo test whether a-amino acids can be efficient chiral auxiliaries in asymmetric Diels-Alder reactions, the chiral dienophile N-acryloyl-L-phenylalanine methyl ester was made to react with cyclopentadiene. Diastereofacial selectivity is to a great extent dependent on the Lewis acid used to promote the reaction; whereas moderate excesses of the (1 R, 2R)-cycloadduct were achieved with AlC13, the reaction did not show diastereofacial selectivity when titanium catalysts were used. Moreover, with T~('PI-(I)4a transesterification reaction, which leads to the isopropyl ester and competes with the Diels-Alder reaction, was observed. In spite of the structural similarity of this dienophile to the acrylate of (S)-ethyl lactate, it behaved very differently in the titanium-catalyzed reactions.This research was made possible by the generous financial support of the Comisión Asesora de Investigación Cientifica y Técnica (project number PB85-0335). Maria P. Bueno would like to express her gratitude to the Diputación General de Aragón and Paula Charro to the Instituto de Estudios Riojanos for a grant.Peer reviewedCanadian Science PublishingComisión Asesora de Investigación Científica y Técnica, CAICYT (España)Gobierno de AragónInstituto de Estudios RiojanosConsejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]201820181988info:eu-repo/semantics/articlehttp://purl.org/coar/resource_type/c_6501Postprintinfo:eu-repo/semantics/acceptedVersionhttp://hdl.handle.net/10261/167788reponame:DIGITAL.CSIC. Repositorio Institucional del CSICinstname:Consejo Superior de Investigaciones Científicas (CSIC)Ingléshttp://dx.doi.org/10.1139/v88-437Síinfo:eu-repo/semantics/openAccessoai:digital.csic.es:10261/1677882026-05-22T06:33:51Z
dc.title.none.fl_str_mv Natural amino acids as chiral auxiliaries in asymmetric Diels-Alder reactions
title Natural amino acids as chiral auxiliaries in asymmetric Diels-Alder reactions
spellingShingle Natural amino acids as chiral auxiliaries in asymmetric Diels-Alder reactions
Bueno, María P.
title_short Natural amino acids as chiral auxiliaries in asymmetric Diels-Alder reactions
title_full Natural amino acids as chiral auxiliaries in asymmetric Diels-Alder reactions
title_fullStr Natural amino acids as chiral auxiliaries in asymmetric Diels-Alder reactions
title_full_unstemmed Natural amino acids as chiral auxiliaries in asymmetric Diels-Alder reactions
title_sort Natural amino acids as chiral auxiliaries in asymmetric Diels-Alder reactions
dc.creator.none.fl_str_mv Bueno, María P.
Cativiela, Carlos
Mayoral, José A.
Avenoza, Alberto
Charro, Paula
Roy, Miguel A.
Andrés Gimeno, José Manuel
author Bueno, María P.
author_facet Bueno, María P.
Cativiela, Carlos
Mayoral, José A.
Avenoza, Alberto
Charro, Paula
Roy, Miguel A.
Andrés Gimeno, José Manuel
author_role author
author2 Cativiela, Carlos
Mayoral, José A.
Avenoza, Alberto
Charro, Paula
Roy, Miguel A.
Andrés Gimeno, José Manuel
author2_role author
author
author
author
author
author
dc.contributor.none.fl_str_mv Comisión Asesora de Investigación Científica y Técnica, CAICYT (España)
Gobierno de Aragón
Instituto de Estudios Riojanos
Consejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]
description To test whether a-amino acids can be efficient chiral auxiliaries in asymmetric Diels-Alder reactions, the chiral dienophile N-acryloyl-L-phenylalanine methyl ester was made to react with cyclopentadiene. Diastereofacial selectivity is to a great extent dependent on the Lewis acid used to promote the reaction; whereas moderate excesses of the (1 R, 2R)-cycloadduct were achieved with AlC13, the reaction did not show diastereofacial selectivity when titanium catalysts were used. Moreover, with T~('PI-(I)4a transesterification reaction, which leads to the isopropyl ester and competes with the Diels-Alder reaction, was observed. In spite of the structural similarity of this dienophile to the acrylate of (S)-ethyl lactate, it behaved very differently in the titanium-catalyzed reactions.
publishDate 1988
dc.date.none.fl_str_mv 1988
2018
2018
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/10261/167788
url http://hdl.handle.net/10261/167788
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv http://dx.doi.org/10.1139/v88-437
Sí
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.publisher.none.fl_str_mv Canadian Science Publishing
publisher.none.fl_str_mv Canadian Science Publishing
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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