2‐Hydroxybenzophenone as a Chemical Auxiliary for the Activation of Ketiminoesters for Highly Enantioselective Addition to Nitroalkenes under Bifunctional Catalysis

An organocatalytic system is presented for the Michael addition of monoactivated glycine ketimine ylides with a bifunctional catalyst. The ketimine bears an ortho hydroxy group, which increases the acidity of the methylene hydrogen atoms and enhances the reactivity, thus allowing the synthesis of a...

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Autores principales: Guerrero‐Corella, Andrea, Esteban, Francisco, Iniesta, Manuel, Martín‐Somer, Ana, Parra, Mario, Díaz‐Tendero, Sergio, Fraile, Alberto, Alemán, Jose
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2018
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5947601/
https://www.ncbi.nlm.nih.gov/pubmed/29493860
http://dx.doi.org/10.1002/anie.201800435
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author Guerrero‐Corella, Andrea
Esteban, Francisco
Iniesta, Manuel
Martín‐Somer, Ana
Parra, Mario
Díaz‐Tendero, Sergio
Fraile, Alberto
Alemán, Jose
author_facet Guerrero‐Corella, Andrea
Esteban, Francisco
Iniesta, Manuel
Martín‐Somer, Ana
Parra, Mario
Díaz‐Tendero, Sergio
Fraile, Alberto
Alemán, Jose
author_sort Guerrero‐Corella, Andrea
collection PubMed
description An organocatalytic system is presented for the Michael addition of monoactivated glycine ketimine ylides with a bifunctional catalyst. The ketimine bears an ortho hydroxy group, which increases the acidity of the methylene hydrogen atoms and enhances the reactivity, thus allowing the synthesis of a large variety of α,γ‐diamino acid derivatives with excellent stereoselectivity.
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spelling pubmed-59476012018-05-17 2‐Hydroxybenzophenone as a Chemical Auxiliary for the Activation of Ketiminoesters for Highly Enantioselective Addition to Nitroalkenes under Bifunctional Catalysis Guerrero‐Corella, Andrea Esteban, Francisco Iniesta, Manuel Martín‐Somer, Ana Parra, Mario Díaz‐Tendero, Sergio Fraile, Alberto Alemán, Jose Angew Chem Int Ed Engl Communications An organocatalytic system is presented for the Michael addition of monoactivated glycine ketimine ylides with a bifunctional catalyst. The ketimine bears an ortho hydroxy group, which increases the acidity of the methylene hydrogen atoms and enhances the reactivity, thus allowing the synthesis of a large variety of α,γ‐diamino acid derivatives with excellent stereoselectivity. John Wiley and Sons Inc. 2018-04-14 2018-05-04 /pmc/articles/PMC5947601/ /pubmed/29493860 http://dx.doi.org/10.1002/anie.201800435 Text en © 2018 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the http://creativecommons.org/licenses/by-nc/4.0/ License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited and is not used for commercial purposes.
spellingShingle Communications
Guerrero‐Corella, Andrea
Esteban, Francisco
Iniesta, Manuel
Martín‐Somer, Ana
Parra, Mario
Díaz‐Tendero, Sergio
Fraile, Alberto
Alemán, Jose
2‐Hydroxybenzophenone as a Chemical Auxiliary for the Activation of Ketiminoesters for Highly Enantioselective Addition to Nitroalkenes under Bifunctional Catalysis
title 2‐Hydroxybenzophenone as a Chemical Auxiliary for the Activation of Ketiminoesters for Highly Enantioselective Addition to Nitroalkenes under Bifunctional Catalysis
title_full 2‐Hydroxybenzophenone as a Chemical Auxiliary for the Activation of Ketiminoesters for Highly Enantioselective Addition to Nitroalkenes under Bifunctional Catalysis
title_fullStr 2‐Hydroxybenzophenone as a Chemical Auxiliary for the Activation of Ketiminoesters for Highly Enantioselective Addition to Nitroalkenes under Bifunctional Catalysis
title_full_unstemmed 2‐Hydroxybenzophenone as a Chemical Auxiliary for the Activation of Ketiminoesters for Highly Enantioselective Addition to Nitroalkenes under Bifunctional Catalysis
title_short 2‐Hydroxybenzophenone as a Chemical Auxiliary for the Activation of Ketiminoesters for Highly Enantioselective Addition to Nitroalkenes under Bifunctional Catalysis
title_sort 2‐hydroxybenzophenone as a chemical auxiliary for the activation of ketiminoesters for highly enantioselective addition to nitroalkenes under bifunctional catalysis
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5947601/
https://www.ncbi.nlm.nih.gov/pubmed/29493860
http://dx.doi.org/10.1002/anie.201800435
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