Stereoselective α-Chlorination of β-Keto Esters in the Presence of Hybrid Amide-Based Cinchona Alkaloids as Catalysts

[Image: see text] We report an enantioselective phase transfer α-chlorination of β-keto esters catalyzed by hybrid amide-based Cinchona derivatives. The chlorination process proceeds with proper quantitative yields (up to <99%) and high asymmetric induction (up to 97% ee). We show that the use of...

Descripción completa

Detalles Bibliográficos
Autores principales: Majdecki, Maciej, Grodek, Piotr, Jurczak, Janusz
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2020
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7872425/
https://www.ncbi.nlm.nih.gov/pubmed/33320665
http://dx.doi.org/10.1021/acs.joc.0c02486
_version_ 1783649182934892544
author Majdecki, Maciej
Grodek, Piotr
Jurczak, Janusz
author_facet Majdecki, Maciej
Grodek, Piotr
Jurczak, Janusz
author_sort Majdecki, Maciej
collection PubMed
description [Image: see text] We report an enantioselective phase transfer α-chlorination of β-keto esters catalyzed by hybrid amide-based Cinchona derivatives. The chlorination process proceeds with proper quantitative yields (up to <99%) and high asymmetric induction (up to 97% ee). We show that the use of only 0.5 mol % hybrid catalyst based on a Cinchona core allows the chlorination reaction to be conducted in a highly enantioselective manner with various indanone and tetralone carboxylate esters.
format Online
Article
Text
id pubmed-7872425
institution National Center for Biotechnology Information
language English
publishDate 2020
publisher American Chemical Society
record_format MEDLINE/PubMed
spelling pubmed-78724252021-02-10 Stereoselective α-Chlorination of β-Keto Esters in the Presence of Hybrid Amide-Based Cinchona Alkaloids as Catalysts Majdecki, Maciej Grodek, Piotr Jurczak, Janusz J Org Chem [Image: see text] We report an enantioselective phase transfer α-chlorination of β-keto esters catalyzed by hybrid amide-based Cinchona derivatives. The chlorination process proceeds with proper quantitative yields (up to <99%) and high asymmetric induction (up to 97% ee). We show that the use of only 0.5 mol % hybrid catalyst based on a Cinchona core allows the chlorination reaction to be conducted in a highly enantioselective manner with various indanone and tetralone carboxylate esters. American Chemical Society 2020-12-15 2021-01-01 /pmc/articles/PMC7872425/ /pubmed/33320665 http://dx.doi.org/10.1021/acs.joc.0c02486 Text en © 2020 American Chemical Society This is an open access article published under a Creative Commons Attribution (CC-BY) License (http://pubs.acs.org/page/policy/authorchoice_ccby_termsofuse.html) , which permits unrestricted use, distribution and reproduction in any medium, provided the author and source are cited.
spellingShingle Majdecki, Maciej
Grodek, Piotr
Jurczak, Janusz
Stereoselective α-Chlorination of β-Keto Esters in the Presence of Hybrid Amide-Based Cinchona Alkaloids as Catalysts
title Stereoselective α-Chlorination of β-Keto Esters in the Presence of Hybrid Amide-Based Cinchona Alkaloids as Catalysts
title_full Stereoselective α-Chlorination of β-Keto Esters in the Presence of Hybrid Amide-Based Cinchona Alkaloids as Catalysts
title_fullStr Stereoselective α-Chlorination of β-Keto Esters in the Presence of Hybrid Amide-Based Cinchona Alkaloids as Catalysts
title_full_unstemmed Stereoselective α-Chlorination of β-Keto Esters in the Presence of Hybrid Amide-Based Cinchona Alkaloids as Catalysts
title_short Stereoselective α-Chlorination of β-Keto Esters in the Presence of Hybrid Amide-Based Cinchona Alkaloids as Catalysts
title_sort stereoselective α-chlorination of β-keto esters in the presence of hybrid amide-based cinchona alkaloids as catalysts
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7872425/
https://www.ncbi.nlm.nih.gov/pubmed/33320665
http://dx.doi.org/10.1021/acs.joc.0c02486
work_keys_str_mv AT majdeckimaciej stereoselectiveachlorinationofbketoestersinthepresenceofhybridamidebasedcinchonaalkaloidsascatalysts
AT grodekpiotr stereoselectiveachlorinationofbketoestersinthepresenceofhybridamidebasedcinchonaalkaloidsascatalysts
AT jurczakjanusz stereoselectiveachlorinationofbketoestersinthepresenceofhybridamidebasedcinchonaalkaloidsascatalysts

Ejemplares similares