Chiral Brønsted acid-catalyzed enantioselective Friedel–Crafts reaction of 2-methoxyfuran with aliphatic ketimines generated in situ

An enantioselective Friedel–Crafts reaction with aliphatic ketimines generated in situ from hemiaminal ethers catalyzed by a chiral Brønsted acid was investigated. The reaction of 2-methoxyfuran with (thio)hydantoin-derived hemiaminal methyl ether proceeded under the influence of a chiral phosphoric...

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Autores principales: Kondoh, Azusa, Ota, Yusuke, Komuro, Takazumi, Egawa, Fuyuki, Kanomata, Kyohei, Terada, Masahiro
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2016
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5952551/
https://www.ncbi.nlm.nih.gov/pubmed/29862000
http://dx.doi.org/10.1039/c5sc03175c
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author Kondoh, Azusa
Ota, Yusuke
Komuro, Takazumi
Egawa, Fuyuki
Kanomata, Kyohei
Terada, Masahiro
author_facet Kondoh, Azusa
Ota, Yusuke
Komuro, Takazumi
Egawa, Fuyuki
Kanomata, Kyohei
Terada, Masahiro
author_sort Kondoh, Azusa
collection PubMed
description An enantioselective Friedel–Crafts reaction with aliphatic ketimines generated in situ from hemiaminal ethers catalyzed by a chiral Brønsted acid was investigated. The reaction of 2-methoxyfuran with (thio)hydantoin-derived hemiaminal methyl ether proceeded under the influence of a chiral phosphoric acid catalyst to afford the corresponding adduct possessing a quaternary stereogenic center in high yield with high enantioselectivity. Theoretical studies were also conducted to clarify the mechanism of the stereochemical outcome and the major factors contributing to the efficient enantioselection.
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spelling pubmed-59525512018-06-01 Chiral Brønsted acid-catalyzed enantioselective Friedel–Crafts reaction of 2-methoxyfuran with aliphatic ketimines generated in situ Kondoh, Azusa Ota, Yusuke Komuro, Takazumi Egawa, Fuyuki Kanomata, Kyohei Terada, Masahiro Chem Sci Chemistry An enantioselective Friedel–Crafts reaction with aliphatic ketimines generated in situ from hemiaminal ethers catalyzed by a chiral Brønsted acid was investigated. The reaction of 2-methoxyfuran with (thio)hydantoin-derived hemiaminal methyl ether proceeded under the influence of a chiral phosphoric acid catalyst to afford the corresponding adduct possessing a quaternary stereogenic center in high yield with high enantioselectivity. Theoretical studies were also conducted to clarify the mechanism of the stereochemical outcome and the major factors contributing to the efficient enantioselection. Royal Society of Chemistry 2016-02-01 2015-10-30 /pmc/articles/PMC5952551/ /pubmed/29862000 http://dx.doi.org/10.1039/c5sc03175c Text en This journal is © The Royal Society of Chemistry 2016 https://creativecommons.org/licenses/by-nc/3.0/This article is freely available. This article is licensed under a Creative Commons Attribution Non Commercial 3.0 Unported Licence (CC BY-NC 3.0)
spellingShingle Chemistry
Kondoh, Azusa
Ota, Yusuke
Komuro, Takazumi
Egawa, Fuyuki
Kanomata, Kyohei
Terada, Masahiro
Chiral Brønsted acid-catalyzed enantioselective Friedel–Crafts reaction of 2-methoxyfuran with aliphatic ketimines generated in situ
title Chiral Brønsted acid-catalyzed enantioselective Friedel–Crafts reaction of 2-methoxyfuran with aliphatic ketimines generated in situ
title_full Chiral Brønsted acid-catalyzed enantioselective Friedel–Crafts reaction of 2-methoxyfuran with aliphatic ketimines generated in situ
title_fullStr Chiral Brønsted acid-catalyzed enantioselective Friedel–Crafts reaction of 2-methoxyfuran with aliphatic ketimines generated in situ
title_full_unstemmed Chiral Brønsted acid-catalyzed enantioselective Friedel–Crafts reaction of 2-methoxyfuran with aliphatic ketimines generated in situ
title_short Chiral Brønsted acid-catalyzed enantioselective Friedel–Crafts reaction of 2-methoxyfuran with aliphatic ketimines generated in situ
title_sort chiral brønsted acid-catalyzed enantioselective friedel–crafts reaction of 2-methoxyfuran with aliphatic ketimines generated in situ
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5952551/
https://www.ncbi.nlm.nih.gov/pubmed/29862000
http://dx.doi.org/10.1039/c5sc03175c
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