Computer-aided insight into the relative stability of enamines

Venerable aldol, Michael, and Mannich reactions have undergone a renaissance in the past fifteen years, as a consequence of the development of direct organocatalytic versions, mediated by chiral amines. Chiral enamines are key intermediates in these reactions. This review focuses on the formation of...

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Autores: Castro Álvarez, Alejandro, Carneros García, Héctor, Costa i Arnau, Anna M., Vilarrasa i Llorens, Jaume
Tipo de recurso: artículo
Estado:Versión aceptada para publicación
Fecha de publicación:2017
País:España
Institución:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
Repositorio:Recercat. Dipósit de la Recerca de Catalunya
OAI Identifier:oai:recercat.cat:2445/154827
Acceso en línea:https://hdl.handle.net/2445/154827
Access Level:acceso abierto
Palabra clave:Enamines
Reaccions d'addició
Reacció aldòlica
Catàlisi heterogènia
Addition reactions
Aldol reaction
Heterogeneus catalysis
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spelling Computer-aided insight into the relative stability of enaminesCastro Álvarez, AlejandroCarneros García, HéctorCosta i Arnau, Anna M.Vilarrasa i Llorens, JaumeEnaminesReaccions d'addicióReacció aldòlicaCatàlisi heterogèniaEnaminesAddition reactionsAldol reactionHeterogeneus catalysisVenerable aldol, Michael, and Mannich reactions have undergone a renaissance in the past fifteen years, as a consequence of the development of direct organocatalytic versions, mediated by chiral amines. Chiral enamines are key intermediates in these reactions. This review focuses on the formation of enamines from secondary amines and their relative thermodynamic stability, as well as on the reverse reactions (hydrolysis). Experimental results and predictions based on MO calculations are reviewed to show which enamine forms may predominate in the reaction medium and to compare several secondary amines as organocatalysts.1 Introduction2 Relative Stability of Enamines as Determined Experimentally3 Pyrrolidine Enamines4 Enamines of the Jorgensen-Hayashi Catalyst5 Proline Enamines6 Free Enthalpies and Polar Solvent Effects7 Comparison of Organocatalysts8 Summary and Outlook9 AppendixGeorg Thieme Verlag2020202020172020info:eu-repo/semantics/articleinfo:eu-repo/semantics/acceptedVersion22 p.application/pdfapplication/pdfhttps://hdl.handle.net/2445/154827Articles publicats en revistes (Química Inorgànica i Orgànica)reponame:Recercat. Dipósit de la Recerca de Catalunyainstname:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)InglésVersió postprint del document publicat a: https://doi.org/10.1055/s-0036-1590909Synthesis. Journal of Synthetic Organic Chemistry, 2017, vol. 49, num. 24, p. 5285-5306https://doi.org/10.1055/s-0036-1590909(c) Georg Thieme Verlag, 2017info:eu-repo/semantics/openAccessoai:recercat.cat:2445/1548272026-05-29T05:05:01Z
dc.title.none.fl_str_mv Computer-aided insight into the relative stability of enamines
title Computer-aided insight into the relative stability of enamines
spellingShingle Computer-aided insight into the relative stability of enamines
Castro Álvarez, Alejandro
Enamines
Reaccions d'addició
Reacció aldòlica
Catàlisi heterogènia
Enamines
Addition reactions
Aldol reaction
Heterogeneus catalysis
title_short Computer-aided insight into the relative stability of enamines
title_full Computer-aided insight into the relative stability of enamines
title_fullStr Computer-aided insight into the relative stability of enamines
title_full_unstemmed Computer-aided insight into the relative stability of enamines
title_sort Computer-aided insight into the relative stability of enamines
dc.creator.none.fl_str_mv Castro Álvarez, Alejandro
Carneros García, Héctor
Costa i Arnau, Anna M.
Vilarrasa i Llorens, Jaume
author Castro Álvarez, Alejandro
author_facet Castro Álvarez, Alejandro
Carneros García, Héctor
Costa i Arnau, Anna M.
Vilarrasa i Llorens, Jaume
author_role author
author2 Carneros García, Héctor
Costa i Arnau, Anna M.
Vilarrasa i Llorens, Jaume
author2_role author
author
author
dc.subject.none.fl_str_mv Enamines
Reaccions d'addició
Reacció aldòlica
Catàlisi heterogènia
Enamines
Addition reactions
Aldol reaction
Heterogeneus catalysis
topic Enamines
Reaccions d'addició
Reacció aldòlica
Catàlisi heterogènia
Enamines
Addition reactions
Aldol reaction
Heterogeneus catalysis
description Venerable aldol, Michael, and Mannich reactions have undergone a renaissance in the past fifteen years, as a consequence of the development of direct organocatalytic versions, mediated by chiral amines. Chiral enamines are key intermediates in these reactions. This review focuses on the formation of enamines from secondary amines and their relative thermodynamic stability, as well as on the reverse reactions (hydrolysis). Experimental results and predictions based on MO calculations are reviewed to show which enamine forms may predominate in the reaction medium and to compare several secondary amines as organocatalysts.1 Introduction2 Relative Stability of Enamines as Determined Experimentally3 Pyrrolidine Enamines4 Enamines of the Jorgensen-Hayashi Catalyst5 Proline Enamines6 Free Enthalpies and Polar Solvent Effects7 Comparison of Organocatalysts8 Summary and Outlook9 Appendix
publishDate 2017
dc.date.none.fl_str_mv 2017
2020
2020
2020
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/acceptedVersion
format article
status_str acceptedVersion
dc.identifier.none.fl_str_mv https://hdl.handle.net/2445/154827
url https://hdl.handle.net/2445/154827
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv Versió postprint del document publicat a: https://doi.org/10.1055/s-0036-1590909
Synthesis. Journal of Synthetic Organic Chemistry, 2017, vol. 49, num. 24, p. 5285-5306
https://doi.org/10.1055/s-0036-1590909
dc.rights.none.fl_str_mv (c) Georg Thieme Verlag, 2017
info:eu-repo/semantics/openAccess
rights_invalid_str_mv (c) Georg Thieme Verlag, 2017
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv 22 p.
application/pdf
application/pdf
dc.publisher.none.fl_str_mv Georg Thieme Verlag
publisher.none.fl_str_mv Georg Thieme Verlag
dc.source.none.fl_str_mv Articles publicats en revistes (Química Inorgànica i Orgànica)
reponame:Recercat. Dipósit de la Recerca de Catalunya
instname:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
instname_str Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
reponame_str Recercat. Dipósit de la Recerca de Catalunya
collection Recercat. Dipósit de la Recerca de Catalunya
repository.name.fl_str_mv
repository.mail.fl_str_mv
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