Catalytic Asymmetric 1,4-Additions of β-Keto Esters to Nitroalkenes Promoted by a Bifunctional Homobimetallic Co(2)-Schiff Base Complex

Catalytic asymmetric 1,4-addition of β-keto esters to nitroalkenes is described. 2.5 mol % of a homobimetallic Lewis acid/Brønsted base bifunctional Co(2)-Schiff base complex smoothly promoted the reaction in excellent yield (up to 99%), diastereoselectivity, and enantioselectivity (up to >30:1 d...

Descripción completa

Detalles Bibliográficos
Autores principales: Furutachi, Makoto, Chen, Zhihua, Matsunaga, Shigeki, Shibasaki, Masakatsu
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Molecular Diversity Preservation International 2010
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6256980/
https://www.ncbi.nlm.nih.gov/pubmed/20110907
http://dx.doi.org/10.3390/molecules15010532
_version_ 1783374248126971904
author Furutachi, Makoto
Chen, Zhihua
Matsunaga, Shigeki
Shibasaki, Masakatsu
author_facet Furutachi, Makoto
Chen, Zhihua
Matsunaga, Shigeki
Shibasaki, Masakatsu
author_sort Furutachi, Makoto
collection PubMed
description Catalytic asymmetric 1,4-addition of β-keto esters to nitroalkenes is described. 2.5 mol % of a homobimetallic Lewis acid/Brønsted base bifunctional Co(2)-Schiff base complex smoothly promoted the reaction in excellent yield (up to 99%), diastereoselectivity, and enantioselectivity (up to >30:1 dr and 98% ee). Catalyst loading was successfully reduced to 0.1 mol %. Mechanistic studies suggested that intramolecular cooperative functions of the two Co-metal centers are important for high catalytic activity and stereoselectivity.
format Online
Article
Text
id pubmed-6256980
institution National Center for Biotechnology Information
language English
publishDate 2010
publisher Molecular Diversity Preservation International
record_format MEDLINE/PubMed
spelling pubmed-62569802018-12-03 Catalytic Asymmetric 1,4-Additions of β-Keto Esters to Nitroalkenes Promoted by a Bifunctional Homobimetallic Co(2)-Schiff Base Complex Furutachi, Makoto Chen, Zhihua Matsunaga, Shigeki Shibasaki, Masakatsu Molecules Article Catalytic asymmetric 1,4-addition of β-keto esters to nitroalkenes is described. 2.5 mol % of a homobimetallic Lewis acid/Brønsted base bifunctional Co(2)-Schiff base complex smoothly promoted the reaction in excellent yield (up to 99%), diastereoselectivity, and enantioselectivity (up to >30:1 dr and 98% ee). Catalyst loading was successfully reduced to 0.1 mol %. Mechanistic studies suggested that intramolecular cooperative functions of the two Co-metal centers are important for high catalytic activity and stereoselectivity. Molecular Diversity Preservation International 2010-01-22 /pmc/articles/PMC6256980/ /pubmed/20110907 http://dx.doi.org/10.3390/molecules15010532 Text en © 2010 by the authors; http://creativecommons.org/licenses/by/3.0/ licensee Molecular Diversity Preservation International, Basel, Switzerland. This article is an open-access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/).
spellingShingle Article
Furutachi, Makoto
Chen, Zhihua
Matsunaga, Shigeki
Shibasaki, Masakatsu
Catalytic Asymmetric 1,4-Additions of β-Keto Esters to Nitroalkenes Promoted by a Bifunctional Homobimetallic Co(2)-Schiff Base Complex
title Catalytic Asymmetric 1,4-Additions of β-Keto Esters to Nitroalkenes Promoted by a Bifunctional Homobimetallic Co(2)-Schiff Base Complex
title_full Catalytic Asymmetric 1,4-Additions of β-Keto Esters to Nitroalkenes Promoted by a Bifunctional Homobimetallic Co(2)-Schiff Base Complex
title_fullStr Catalytic Asymmetric 1,4-Additions of β-Keto Esters to Nitroalkenes Promoted by a Bifunctional Homobimetallic Co(2)-Schiff Base Complex
title_full_unstemmed Catalytic Asymmetric 1,4-Additions of β-Keto Esters to Nitroalkenes Promoted by a Bifunctional Homobimetallic Co(2)-Schiff Base Complex
title_short Catalytic Asymmetric 1,4-Additions of β-Keto Esters to Nitroalkenes Promoted by a Bifunctional Homobimetallic Co(2)-Schiff Base Complex
title_sort catalytic asymmetric 1,4-additions of β-keto esters to nitroalkenes promoted by a bifunctional homobimetallic co(2)-schiff base complex
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6256980/
https://www.ncbi.nlm.nih.gov/pubmed/20110907
http://dx.doi.org/10.3390/molecules15010532
work_keys_str_mv AT furutachimakoto catalyticasymmetric14additionsofbketoesterstonitroalkenespromotedbyabifunctionalhomobimetallicco2schiffbasecomplex
AT chenzhihua catalyticasymmetric14additionsofbketoesterstonitroalkenespromotedbyabifunctionalhomobimetallicco2schiffbasecomplex
AT matsunagashigeki catalyticasymmetric14additionsofbketoesterstonitroalkenespromotedbyabifunctionalhomobimetallicco2schiffbasecomplex
AT shibasakimasakatsu catalyticasymmetric14additionsofbketoesterstonitroalkenespromotedbyabifunctionalhomobimetallicco2schiffbasecomplex

Ejemplares similares