The use of 1-amino-2-phenyl-1-cyclohexanecarboxylic acids as chiral auxiliaries in asymmetric Diels-Alder reactions

This report describes the behavior of four 1-amino-2-phenyl-1-cyclohexanecarboxylic acids, obtained in enantiomerically pure form starting from asymmetric Diels-Alder reactions between 1,3-butadiene and chiral (E)-2-cyanocinnamates, as chiral auxiliaries in the asymmetric Diels-Alder reactions of cy...

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Autores: Avenoza, A. [0000-0002-5465-3555], Cativiela, C., París, M., Peregrina, J.M. [0000-0003-3778-7065]
Tipo de recurso: artículo
Estado:Versión publicada
Fecha de publicación:1996
País:España
Institución:Universidad de La Rioja (UR)
Repositorio:RIUR. Repositorio Institucional de la Universidad de La Rioja
OAI Identifier:oai:portal.dialnet.es:doc/5bbc68feb750603269e81317
Acceso en línea:https://investigacion.unirioja.es/documentos/5bbc68feb750603269e81317
Access Level:acceso abierto
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spelling The use of 1-amino-2-phenyl-1-cyclohexanecarboxylic acids as chiral auxiliaries in asymmetric Diels-Alder reactionsAvenoza, A. [0000-0002-5465-3555]Cativiela, C.París, M.Peregrina, J.M. [0000-0003-3778-7065]This report describes the behavior of four 1-amino-2-phenyl-1-cyclohexanecarboxylic acids, obtained in enantiomerically pure form starting from asymmetric Diels-Alder reactions between 1,3-butadiene and chiral (E)-2-cyanocinnamates, as chiral auxiliaries in the asymmetric Diels-Alder reactions of cyclopentadiene with chiral methyl N-acryloyl-1-amino-2-phenyl-1-cyclohexane-carboxylates. A model based on the formation of an intramolecular hydrogen bond accounts for the stereochemical outcome in the catalyzed reactions.1996info:eu-repo/semantics/articleSubtype: Articleinfo:eu-repo/semantics/publishedVersionapplication/pdfhttps://investigacion.unirioja.es/documentos/5bbc68feb750603269e81317reponame:RIUR. Repositorio Institucional de la Universidad de La Riojainstname:Universidad de La Rioja (UR)Inglésinfo:eu-repo/semantics/altIdentifier/doi/10.1016/0040-4020(96)00155-Xinfo:eu-repo/semantics/altIdentifier/wos/WOS:A1996UC44300024info:eu-repo/semantics/altIdentifier/pissn/0040-4020The use of 1-amino-2-phenyl-1-cyclohexanecarboxylic acids as chiral auxiliaries in asymmetric Diels-Alder reactions, 1996, vol. 52, núm. 13, pág. 4839-4848info:eu-repo/semantics/openAccessoai:portal.dialnet.es:doc/5bbc68feb750603269e813172026-06-14T12:47:17Z
dc.title.none.fl_str_mv The use of 1-amino-2-phenyl-1-cyclohexanecarboxylic acids as chiral auxiliaries in asymmetric Diels-Alder reactions
title The use of 1-amino-2-phenyl-1-cyclohexanecarboxylic acids as chiral auxiliaries in asymmetric Diels-Alder reactions
spellingShingle The use of 1-amino-2-phenyl-1-cyclohexanecarboxylic acids as chiral auxiliaries in asymmetric Diels-Alder reactions
Avenoza, A. [0000-0002-5465-3555]
title_short The use of 1-amino-2-phenyl-1-cyclohexanecarboxylic acids as chiral auxiliaries in asymmetric Diels-Alder reactions
title_full The use of 1-amino-2-phenyl-1-cyclohexanecarboxylic acids as chiral auxiliaries in asymmetric Diels-Alder reactions
title_fullStr The use of 1-amino-2-phenyl-1-cyclohexanecarboxylic acids as chiral auxiliaries in asymmetric Diels-Alder reactions
title_full_unstemmed The use of 1-amino-2-phenyl-1-cyclohexanecarboxylic acids as chiral auxiliaries in asymmetric Diels-Alder reactions
title_sort The use of 1-amino-2-phenyl-1-cyclohexanecarboxylic acids as chiral auxiliaries in asymmetric Diels-Alder reactions
dc.creator.none.fl_str_mv Avenoza, A. [0000-0002-5465-3555]
Cativiela, C.
París, M.
Peregrina, J.M. [0000-0003-3778-7065]
author Avenoza, A. [0000-0002-5465-3555]
author_facet Avenoza, A. [0000-0002-5465-3555]
Cativiela, C.
París, M.
Peregrina, J.M. [0000-0003-3778-7065]
author_role author
author2 Cativiela, C.
París, M.
Peregrina, J.M. [0000-0003-3778-7065]
author2_role author
author
author
description This report describes the behavior of four 1-amino-2-phenyl-1-cyclohexanecarboxylic acids, obtained in enantiomerically pure form starting from asymmetric Diels-Alder reactions between 1,3-butadiene and chiral (E)-2-cyanocinnamates, as chiral auxiliaries in the asymmetric Diels-Alder reactions of cyclopentadiene with chiral methyl N-acryloyl-1-amino-2-phenyl-1-cyclohexane-carboxylates. A model based on the formation of an intramolecular hydrogen bond accounts for the stereochemical outcome in the catalyzed reactions.
publishDate 1996
dc.date.none.fl_str_mv 1996
dc.type.none.fl_str_mv info:eu-repo/semantics/article
Subtype: Article
info:eu-repo/semantics/publishedVersion
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv https://investigacion.unirioja.es/documentos/5bbc68feb750603269e81317
url https://investigacion.unirioja.es/documentos/5bbc68feb750603269e81317
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1016/0040-4020(96)00155-X
info:eu-repo/semantics/altIdentifier/wos/WOS:A1996UC44300024
info:eu-repo/semantics/altIdentifier/pissn/0040-4020
The use of 1-amino-2-phenyl-1-cyclohexanecarboxylic acids as chiral auxiliaries in asymmetric Diels-Alder reactions, 1996, vol. 52, núm. 13, pág. 4839-4848
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.source.none.fl_str_mv reponame:RIUR. Repositorio Institucional de la Universidad de La Rioja
instname:Universidad de La Rioja (UR)
instname_str Universidad de La Rioja (UR)
reponame_str RIUR. Repositorio Institucional de la Universidad de La Rioja
collection RIUR. Repositorio Institucional de la Universidad de La Rioja
repository.name.fl_str_mv
repository.mail.fl_str_mv
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score 15,301603

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