N-Heterocyclic carbene-catalyzed direct cross-aza-benzoin reaction: Efficient synthesis of α-amino-β-keto esters

An efficient catalytic synthesis of α-amino-β-keto esters has been newly developed. Cross-coupling of various aldehydes with α-imino ester, catalyzed by N-heterocyclic carbene, leads chemoselectively to α-amino-β-keto esters in moderate to good yields with high atom efficiency. The reaction mechanis...

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Detalles Bibliográficos
Autores principales: Uno, Takuya, Kobayashi, Yusuke, Takemoto, Yoshiji
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2012
Materias:
Letter
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3458774/
https://www.ncbi.nlm.nih.gov/pubmed/23019484
http://dx.doi.org/10.3762/bjoc.8.169
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author Uno, Takuya
Kobayashi, Yusuke
Takemoto, Yoshiji
author_facet Uno, Takuya
Kobayashi, Yusuke
Takemoto, Yoshiji
author_sort Uno, Takuya
collection PubMed
description An efficient catalytic synthesis of α-amino-β-keto esters has been newly developed. Cross-coupling of various aldehydes with α-imino ester, catalyzed by N-heterocyclic carbene, leads chemoselectively to α-amino-β-keto esters in moderate to good yields with high atom efficiency. The reaction mechanism is discussed, and it is proposed that the α-amino-β-keto esters are formed under thermodynamic control.
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spelling pubmed-34587742012-09-27 N-Heterocyclic carbene-catalyzed direct cross-aza-benzoin reaction: Efficient synthesis of α-amino-β-keto esters Uno, Takuya Kobayashi, Yusuke Takemoto, Yoshiji Beilstein J Org Chem Letter An efficient catalytic synthesis of α-amino-β-keto esters has been newly developed. Cross-coupling of various aldehydes with α-imino ester, catalyzed by N-heterocyclic carbene, leads chemoselectively to α-amino-β-keto esters in moderate to good yields with high atom efficiency. The reaction mechanism is discussed, and it is proposed that the α-amino-β-keto esters are formed under thermodynamic control. Beilstein-Institut 2012-09-10 /pmc/articles/PMC3458774/ /pubmed/23019484 http://dx.doi.org/10.3762/bjoc.8.169 Text en Copyright © 2012, Uno et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Letter
Uno, Takuya
Kobayashi, Yusuke
Takemoto, Yoshiji
N-Heterocyclic carbene-catalyzed direct cross-aza-benzoin reaction: Efficient synthesis of α-amino-β-keto esters
title N-Heterocyclic carbene-catalyzed direct cross-aza-benzoin reaction: Efficient synthesis of α-amino-β-keto esters
title_full N-Heterocyclic carbene-catalyzed direct cross-aza-benzoin reaction: Efficient synthesis of α-amino-β-keto esters
title_fullStr N-Heterocyclic carbene-catalyzed direct cross-aza-benzoin reaction: Efficient synthesis of α-amino-β-keto esters
title_full_unstemmed N-Heterocyclic carbene-catalyzed direct cross-aza-benzoin reaction: Efficient synthesis of α-amino-β-keto esters
title_short N-Heterocyclic carbene-catalyzed direct cross-aza-benzoin reaction: Efficient synthesis of α-amino-β-keto esters
title_sort n-heterocyclic carbene-catalyzed direct cross-aza-benzoin reaction: efficient synthesis of α-amino-β-keto esters
topic Letter
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3458774/
https://www.ncbi.nlm.nih.gov/pubmed/23019484
http://dx.doi.org/10.3762/bjoc.8.169
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