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
Description
Summary: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.
ISSN:1860-5397

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