CO(2)-Assisted asymmetric hydrogenation of prochiral allylamines

A new methodology for the asymmetric hydrogenation of allylamines takes advantage of a reversible reaction between amines and carbon dioxide (CO(2)) to suppress unwanted side reactions. The effects of various parameters (pressure, time, solvent, and base additives) on the enantioselectivity and conv...

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Detalles Bibliográficos
Autores principales: de Winter, Tamara M., Ho, Jaddie, Alridge, Christopher J., Jessop, Philip G.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2022
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8981594/
https://www.ncbi.nlm.nih.gov/pubmed/35424608
http://dx.doi.org/10.1039/d2ra00263a
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author de Winter, Tamara M.
Ho, Jaddie
Alridge, Christopher J.
Jessop, Philip G.
author_facet de Winter, Tamara M.
Ho, Jaddie
Alridge, Christopher J.
Jessop, Philip G.
author_sort de Winter, Tamara M.
collection PubMed
description A new methodology for the asymmetric hydrogenation of allylamines takes advantage of a reversible reaction between amines and carbon dioxide (CO(2)) to suppress unwanted side reactions. The effects of various parameters (pressure, time, solvent, and base additives) on the enantioselectivity and conversion of the reaction were studied. The homogeneously-catalyzed asymmetric hydrogenation of 2-arylprop-2-en-1-amine resulted in complete conversion and up to 82% enantiomeric excess (ee). Added base, if chosen carefully, improves the enantioselectivity and chemoselectivity of the overall reaction.
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spelling pubmed-89815942022-04-13 CO(2)-Assisted asymmetric hydrogenation of prochiral allylamines de Winter, Tamara M. Ho, Jaddie Alridge, Christopher J. Jessop, Philip G. RSC Adv Chemistry A new methodology for the asymmetric hydrogenation of allylamines takes advantage of a reversible reaction between amines and carbon dioxide (CO(2)) to suppress unwanted side reactions. The effects of various parameters (pressure, time, solvent, and base additives) on the enantioselectivity and conversion of the reaction were studied. The homogeneously-catalyzed asymmetric hydrogenation of 2-arylprop-2-en-1-amine resulted in complete conversion and up to 82% enantiomeric excess (ee). Added base, if chosen carefully, improves the enantioselectivity and chemoselectivity of the overall reaction. The Royal Society of Chemistry 2022-02-28 /pmc/articles/PMC8981594/ /pubmed/35424608 http://dx.doi.org/10.1039/d2ra00263a Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by/3.0/
spellingShingle Chemistry
de Winter, Tamara M.
Ho, Jaddie
Alridge, Christopher J.
Jessop, Philip G.
CO(2)-Assisted asymmetric hydrogenation of prochiral allylamines
title CO(2)-Assisted asymmetric hydrogenation of prochiral allylamines
title_full CO(2)-Assisted asymmetric hydrogenation of prochiral allylamines
title_fullStr CO(2)-Assisted asymmetric hydrogenation of prochiral allylamines
title_full_unstemmed CO(2)-Assisted asymmetric hydrogenation of prochiral allylamines
title_short CO(2)-Assisted asymmetric hydrogenation of prochiral allylamines
title_sort co(2)-assisted asymmetric hydrogenation of prochiral allylamines
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8981594/
https://www.ncbi.nlm.nih.gov/pubmed/35424608
http://dx.doi.org/10.1039/d2ra00263a
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