L-proline/cholesterol and diosgenin based thiourea cooperative system for the direct asymmetric aldol reaction in the presence of water

A series of cholesterol and based hydrophobic urea and thiourea compounds were synthesized and successfully used as a cocatalyst for L-proline catalyzed aldol reactions in the presence of water. The anticonfigured products were obtained with good yields (up to 94%), high diastereoselectivities (up...

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Autores principales: EYMUR, Serkan, TAŞCI, Enis, UYANIK, Arzu, YILMAZ, Mustafa
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Scientific and Technological Research Council of Turkey 2020
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7751905/
https://www.ncbi.nlm.nih.gov/pubmed/33488228
http://dx.doi.org/10.3906/kim-2003-36
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author EYMUR, Serkan
TAŞCI, Enis
UYANIK, Arzu
YILMAZ, Mustafa
author_facet EYMUR, Serkan
TAŞCI, Enis
UYANIK, Arzu
YILMAZ, Mustafa
author_sort EYMUR, Serkan
collection PubMed
description A series of cholesterol and based hydrophobic urea and thiourea compounds were synthesized and successfully used as a cocatalyst for L-proline catalyzed aldol reactions in the presence of water. The anticonfigured products were obtained with good yields (up to 94%), high diastereoselectivities (up to 95:5), and high enantiomeric excesses (up to 93% ee ). The successful results for catalytic efficiency of L-proline in the presence of water reveal the importance of the hydrophobic nature of cholesterol and diosgenin parts of thiourea on the reactivity and selectivity in the presence of water.
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spelling pubmed-77519052021-01-22 L-proline/cholesterol and diosgenin based thiourea cooperative system for the direct asymmetric aldol reaction in the presence of water EYMUR, Serkan TAŞCI, Enis UYANIK, Arzu YILMAZ, Mustafa Turk J Chem Article A series of cholesterol and based hydrophobic urea and thiourea compounds were synthesized and successfully used as a cocatalyst for L-proline catalyzed aldol reactions in the presence of water. The anticonfigured products were obtained with good yields (up to 94%), high diastereoselectivities (up to 95:5), and high enantiomeric excesses (up to 93% ee ). The successful results for catalytic efficiency of L-proline in the presence of water reveal the importance of the hydrophobic nature of cholesterol and diosgenin parts of thiourea on the reactivity and selectivity in the presence of water. The Scientific and Technological Research Council of Turkey 2020-10-26 /pmc/articles/PMC7751905/ /pubmed/33488228 http://dx.doi.org/10.3906/kim-2003-36 Text en Copyright © 2020 The Author(s) This article is distributed under the terms of the Creative Commons Attribution License ( http://creativecommons.org/licenses/by/4.0/ ), which permits unrestricted use and redistribution provided that the original author and source are credited.
spellingShingle Article
EYMUR, Serkan
TAŞCI, Enis
UYANIK, Arzu
YILMAZ, Mustafa
L-proline/cholesterol and diosgenin based thiourea cooperative system for the direct asymmetric aldol reaction in the presence of water
title L-proline/cholesterol and diosgenin based thiourea cooperative system for the direct asymmetric aldol reaction in the presence of water
title_full L-proline/cholesterol and diosgenin based thiourea cooperative system for the direct asymmetric aldol reaction in the presence of water
title_fullStr L-proline/cholesterol and diosgenin based thiourea cooperative system for the direct asymmetric aldol reaction in the presence of water
title_full_unstemmed L-proline/cholesterol and diosgenin based thiourea cooperative system for the direct asymmetric aldol reaction in the presence of water
title_short L-proline/cholesterol and diosgenin based thiourea cooperative system for the direct asymmetric aldol reaction in the presence of water
title_sort l-proline/cholesterol and diosgenin based thiourea cooperative system for the direct asymmetric aldol reaction in the presence of water
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7751905/
https://www.ncbi.nlm.nih.gov/pubmed/33488228
http://dx.doi.org/10.3906/kim-2003-36
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