Highly Enantioselective Epoxidation of α,β-Unsaturated Ketones Using Amide-Based Cinchona Alkaloids as Hybrid Phase-Transfer Catalysts

[Image: see text] A series of 20 one chiral epoxides were obtained with excellent yields (up to 99%) and enantioselectivities (up to >99% ee) using hybrid amide-based Cinchona alkaloids. Our method is characterized by low catalyst loading (0.5 mol %) and short reaction times. Moreover, the epoxid...

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Autores principales: Majdecki, Maciej, Tyszka-Gumkowska, Agata, Jurczak, Janusz
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2020
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7660942/
https://www.ncbi.nlm.nih.gov/pubmed/33112627
http://dx.doi.org/10.1021/acs.orglett.0c03272
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author Majdecki, Maciej
Tyszka-Gumkowska, Agata
Jurczak, Janusz
author_facet Majdecki, Maciej
Tyszka-Gumkowska, Agata
Jurczak, Janusz
author_sort Majdecki, Maciej
collection PubMed
description [Image: see text] A series of 20 one chiral epoxides were obtained with excellent yields (up to 99%) and enantioselectivities (up to >99% ee) using hybrid amide-based Cinchona alkaloids. Our method is characterized by low catalyst loading (0.5 mol %) and short reaction times. Moreover, the epoxidation process can be carried out in 10 cycles, without further catalyst addition to the reaction mixture. This methodology significantly enhance the scale of the process using very low catalyst loading.
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spelling pubmed-76609422020-11-13 Highly Enantioselective Epoxidation of α,β-Unsaturated Ketones Using Amide-Based Cinchona Alkaloids as Hybrid Phase-Transfer Catalysts Majdecki, Maciej Tyszka-Gumkowska, Agata Jurczak, Janusz Org Lett [Image: see text] A series of 20 one chiral epoxides were obtained with excellent yields (up to 99%) and enantioselectivities (up to >99% ee) using hybrid amide-based Cinchona alkaloids. Our method is characterized by low catalyst loading (0.5 mol %) and short reaction times. Moreover, the epoxidation process can be carried out in 10 cycles, without further catalyst addition to the reaction mixture. This methodology significantly enhance the scale of the process using very low catalyst loading. American Chemical Society 2020-10-28 2020-11-06 /pmc/articles/PMC7660942/ /pubmed/33112627 http://dx.doi.org/10.1021/acs.orglett.0c03272 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
Tyszka-Gumkowska, Agata
Jurczak, Janusz
Highly Enantioselective Epoxidation of α,β-Unsaturated Ketones Using Amide-Based Cinchona Alkaloids as Hybrid Phase-Transfer Catalysts
title Highly Enantioselective Epoxidation of α,β-Unsaturated Ketones Using Amide-Based Cinchona Alkaloids as Hybrid Phase-Transfer Catalysts
title_full Highly Enantioselective Epoxidation of α,β-Unsaturated Ketones Using Amide-Based Cinchona Alkaloids as Hybrid Phase-Transfer Catalysts
title_fullStr Highly Enantioselective Epoxidation of α,β-Unsaturated Ketones Using Amide-Based Cinchona Alkaloids as Hybrid Phase-Transfer Catalysts
title_full_unstemmed Highly Enantioselective Epoxidation of α,β-Unsaturated Ketones Using Amide-Based Cinchona Alkaloids as Hybrid Phase-Transfer Catalysts
title_short Highly Enantioselective Epoxidation of α,β-Unsaturated Ketones Using Amide-Based Cinchona Alkaloids as Hybrid Phase-Transfer Catalysts
title_sort highly enantioselective epoxidation of α,β-unsaturated ketones using amide-based cinchona alkaloids as hybrid phase-transfer catalysts
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7660942/
https://www.ncbi.nlm.nih.gov/pubmed/33112627
http://dx.doi.org/10.1021/acs.orglett.0c03272
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AT jurczakjanusz highlyenantioselectiveepoxidationofabunsaturatedketonesusingamidebasedcinchonaalkaloidsashybridphasetransfercatalysts

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