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

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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Bibliographic Details
Main Authors: M. Emin Cinar, Bernward Engelen, Martin Panthöfer, Hans-Jörg Deiseroth, Jens Schlirf, Michael Schmittel
Format: Article
Language:English
Published: Beilstein-Institut 2016-04-01
Series:Beilstein Journal of Organic Chemistry
Subjects:
DFT
diastereoselective reaction
domino aldol
metal enolate
tetrahydropyran
Online Access:https://doi.org/10.3762/bjoc.12.80
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spelling doaj-8a0246af030f4f598820ddd91e3837422021-02-02T03:25:48ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972016-04-0112181382410.3762/bjoc.12.801860-5397-12-80Scope and mechanism of the highly stereoselective metal-mediated domino aldol reactions of enolates with aldehydesM. Emin Cinar0Bernward Engelen1Martin Panthöfer2Hans-Jörg Deiseroth3Jens Schlirf4Michael Schmittel5Department Chemie-Biologie, OC1, Universität Siegen, Adolf-Reichwein-Str., D-57068 Siegen, GermanyDepartment Chemie-Biologie, OC1, Universität Siegen, Adolf-Reichwein-Str., D-57068 Siegen, GermanyDepartment Chemie-Biologie, OC1, Universität Siegen, Adolf-Reichwein-Str., D-57068 Siegen, GermanyDepartment Chemie-Biologie, OC1, Universität Siegen, Adolf-Reichwein-Str., D-57068 Siegen, GermanyDepartment Chemie-Biologie, OC1, Universität Siegen, Adolf-Reichwein-Str., D-57068 Siegen, GermanyDepartment Chemie-Biologie, OC1, Universität Siegen, Adolf-Reichwein-Str., D-57068 Siegen, GermanyA 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.https://doi.org/10.3762/bjoc.12.80DFTdiastereoselective reactiondomino aldolmetal enolatetetrahydropyran
collection DOAJ
language English
format Article
sources DOAJ
author M. Emin Cinar
Bernward Engelen
Martin Panthöfer
Hans-Jörg Deiseroth
Jens Schlirf
Michael Schmittel
spellingShingle M. Emin Cinar
Bernward Engelen
Martin Panthöfer
Hans-Jörg Deiseroth
Jens Schlirf
Michael Schmittel
Scope and mechanism of the highly stereoselective metal-mediated domino aldol reactions of enolates with aldehydes
Beilstein Journal of Organic Chemistry
DFT
diastereoselective reaction
domino aldol
metal enolate
tetrahydropyran
author_facet M. Emin Cinar
Bernward Engelen
Martin Panthöfer
Hans-Jörg Deiseroth
Jens Schlirf
Michael Schmittel
author_sort M. Emin Cinar
title 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_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_sort scope and mechanism of the highly stereoselective metal-mediated domino aldol reactions of enolates with aldehydes
publisher Beilstein-Institut
series Beilstein Journal of Organic Chemistry
issn 1860-5397
publishDate 2016-04-01
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.
topic DFT
diastereoselective reaction
domino aldol
metal enolate
tetrahydropyran
url https://doi.org/10.3762/bjoc.12.80
work_keys_str_mv AT memincinar scopeandmechanismofthehighlystereoselectivemetalmediateddominoaldolreactionsofenolateswithaldehydes
AT bernwardengelen scopeandmechanismofthehighlystereoselectivemetalmediateddominoaldolreactionsofenolateswithaldehydes
AT martinpanthofer scopeandmechanismofthehighlystereoselectivemetalmediateddominoaldolreactionsofenolateswithaldehydes
AT hansjorgdeiseroth scopeandmechanismofthehighlystereoselectivemetalmediateddominoaldolreactionsofenolateswithaldehydes
AT jensschlirf scopeandmechanismofthehighlystereoselectivemetalmediateddominoaldolreactionsofenolateswithaldehydes
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