Scope and mechanism of the highly stereoselective metal-mediated domino aldol reactions of enolates with aldehydes

A one-pot transformation, which involves the reaction of ketones with aldehydes in the presence of metal halides to furnish tetrahydro-2H-pyran-2,4-diols in a highly diastereoselective manner, is investigated thoroughly by experiments and computations. The reaction was also successfully implemented...

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Detalles Bibliográficos
Autores principales: Cinar, M Emin, Engelen, Bernward, Panthöfer, Martin, Deiseroth, Hans-Jörg, Schlirf, Jens, Schmittel, Michael
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2016
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4902021/
https://www.ncbi.nlm.nih.gov/pubmed/27340472
http://dx.doi.org/10.3762/bjoc.12.80
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author Cinar, M Emin
Engelen, Bernward
Panthöfer, Martin
Deiseroth, Hans-Jörg
Schlirf, Jens
Schmittel, Michael
author_facet Cinar, M Emin
Engelen, Bernward
Panthöfer, Martin
Deiseroth, Hans-Jörg
Schlirf, Jens
Schmittel, Michael
author_sort Cinar, M Emin
collection PubMed
description A one-pot transformation, which involves the reaction of ketones with aldehydes in the presence of metal halides to furnish tetrahydro-2H-pyran-2,4-diols in a highly diastereoselective manner, is investigated thoroughly by experiments and computations. The reaction was also successfully implemented on a flow micro reactor system.
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spelling pubmed-49020212016-06-23 Scope and mechanism of the highly stereoselective metal-mediated domino aldol reactions of enolates with aldehydes Cinar, M Emin Engelen, Bernward Panthöfer, Martin Deiseroth, Hans-Jörg Schlirf, Jens Schmittel, Michael Beilstein J Org Chem Full Research Paper A one-pot transformation, which involves the reaction of ketones with aldehydes in the presence of metal halides to furnish tetrahydro-2H-pyran-2,4-diols in a highly diastereoselective manner, is investigated thoroughly by experiments and computations. The reaction was also successfully implemented on a flow micro reactor system. Beilstein-Institut 2016-04-27 /pmc/articles/PMC4902021/ /pubmed/27340472 http://dx.doi.org/10.3762/bjoc.12.80 Text en Copyright © 2016, Cinar et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Cinar, M Emin
Engelen, Bernward
Panthöfer, Martin
Deiseroth, Hans-Jörg
Schlirf, Jens
Schmittel, Michael
Scope and mechanism of the highly stereoselective metal-mediated domino aldol reactions of enolates with aldehydes
title Scope and mechanism of the highly stereoselective metal-mediated domino aldol reactions of enolates with aldehydes
title_full Scope and mechanism of the highly stereoselective metal-mediated domino aldol reactions of enolates with aldehydes
title_fullStr Scope and mechanism of the highly stereoselective metal-mediated domino aldol reactions of enolates with aldehydes
title_full_unstemmed Scope and mechanism of the highly stereoselective metal-mediated domino aldol reactions of enolates with aldehydes
title_short Scope and mechanism of the highly stereoselective metal-mediated domino aldol reactions of enolates with aldehydes
title_sort scope and mechanism of the highly stereoselective metal-mediated domino aldol reactions of enolates with aldehydes
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4902021/
https://www.ncbi.nlm.nih.gov/pubmed/27340472
http://dx.doi.org/10.3762/bjoc.12.80
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