Stereoselective Lewis base catalyzed formal 1,3-dipolar cycloaddition of azomethine imines with mixed anhydrides

Stereoselective synthesis of pyrazolidinones via dipolar cycloaddition of azomethine imines with active esters under Lewis base catalysis is presented. The active esters are readily generated in situ from the corresponding acids. Products, which are obtained with excellent diastereocontrol and high...

Descripción completa

Detalles Bibliográficos
Autores principales: Hesping, Lena, Biswas, Anup, Daniliuc, Constantin G., Mück-Lichtenfeld, Christian, Studer, Armido
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2015
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5811128/
https://www.ncbi.nlm.nih.gov/pubmed/29541440
http://dx.doi.org/10.1039/c4sc02612h
_version_ 1783299819731681280
author Hesping, Lena
Biswas, Anup
Daniliuc, Constantin G.
Mück-Lichtenfeld, Christian
Studer, Armido
author_facet Hesping, Lena
Biswas, Anup
Daniliuc, Constantin G.
Mück-Lichtenfeld, Christian
Studer, Armido
author_sort Hesping, Lena
collection PubMed
description Stereoselective synthesis of pyrazolidinones via dipolar cycloaddition of azomethine imines with active esters under Lewis base catalysis is presented. The active esters are readily generated in situ from the corresponding acids. Products, which are obtained with excellent diastereocontrol and high enantioselectivity, contain along with the pyrazolidinone core also the tetrahydroisoquinoline structural motif. Theoretical studies give insight into the mechanism of the formal cycloaddition reaction.
format Online
Article
Text
id pubmed-5811128
institution National Center for Biotechnology Information
language English
publishDate 2015
publisher Royal Society of Chemistry
record_format MEDLINE/PubMed
spelling pubmed-58111282018-03-14 Stereoselective Lewis base catalyzed formal 1,3-dipolar cycloaddition of azomethine imines with mixed anhydrides Hesping, Lena Biswas, Anup Daniliuc, Constantin G. Mück-Lichtenfeld, Christian Studer, Armido Chem Sci Chemistry Stereoselective synthesis of pyrazolidinones via dipolar cycloaddition of azomethine imines with active esters under Lewis base catalysis is presented. The active esters are readily generated in situ from the corresponding acids. Products, which are obtained with excellent diastereocontrol and high enantioselectivity, contain along with the pyrazolidinone core also the tetrahydroisoquinoline structural motif. Theoretical studies give insight into the mechanism of the formal cycloaddition reaction. Royal Society of Chemistry 2015-02-01 2014-11-19 /pmc/articles/PMC5811128/ /pubmed/29541440 http://dx.doi.org/10.1039/c4sc02612h Text en This journal is © The Royal Society of Chemistry 2015 http://creativecommons.org/licenses/by/3.0/ This article is freely available. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence (CC BY 3.0)
spellingShingle Chemistry
Hesping, Lena
Biswas, Anup
Daniliuc, Constantin G.
Mück-Lichtenfeld, Christian
Studer, Armido
Stereoselective Lewis base catalyzed formal 1,3-dipolar cycloaddition of azomethine imines with mixed anhydrides
title Stereoselective Lewis base catalyzed formal 1,3-dipolar cycloaddition of azomethine imines with mixed anhydrides
title_full Stereoselective Lewis base catalyzed formal 1,3-dipolar cycloaddition of azomethine imines with mixed anhydrides
title_fullStr Stereoselective Lewis base catalyzed formal 1,3-dipolar cycloaddition of azomethine imines with mixed anhydrides
title_full_unstemmed Stereoselective Lewis base catalyzed formal 1,3-dipolar cycloaddition of azomethine imines with mixed anhydrides
title_short Stereoselective Lewis base catalyzed formal 1,3-dipolar cycloaddition of azomethine imines with mixed anhydrides
title_sort stereoselective lewis base catalyzed formal 1,3-dipolar cycloaddition of azomethine imines with mixed anhydrides
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5811128/
https://www.ncbi.nlm.nih.gov/pubmed/29541440
http://dx.doi.org/10.1039/c4sc02612h
work_keys_str_mv AT hespinglena stereoselectivelewisbasecatalyzedformal13dipolarcycloadditionofazomethineimineswithmixedanhydrides
AT biswasanup stereoselectivelewisbasecatalyzedformal13dipolarcycloadditionofazomethineimineswithmixedanhydrides
AT daniliucconstanting stereoselectivelewisbasecatalyzedformal13dipolarcycloadditionofazomethineimineswithmixedanhydrides
AT mucklichtenfeldchristian stereoselectivelewisbasecatalyzedformal13dipolarcycloadditionofazomethineimineswithmixedanhydrides
AT studerarmido stereoselectivelewisbasecatalyzedformal13dipolarcycloadditionofazomethineimineswithmixedanhydrides

Ejemplares similares