Issue 80, 2012
From the journal:

Chemical Communications

Enantioselective organocatalytic domino synthesis of tetrahydropyridin-2-ols†

Jie-Ping Wan,ab   Charles C. J. Loh,a   Fangfang Panc  and  Dieter Enders*a  

* Corresponding authors

a Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany
E-mail: enders@rwth-aachen.de
Fax: +49-241-809-2127

b College of Chemistry and Chemical Engineering, Jiangxi Normal University, Nanchang 330022, P.R. China

c Institute of Inorganic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany

Abstract

The asymmetric synthesis of tetrahydropyridin-2-ols from enals and enaminones is described. The organocatalytic domino reaction involves a Michael addition–hemiaminalization sequence using the Jørgensen–Hayashi catalyst. Dehydration or oxidation leads to the corresponding 1,4-dihydro-pyridines or 3,4-dihydropyridin-2-ones in a one-pot fashion.

Graphical abstract: Enantioselective organocatalytic domino synthesis of tetrahydropyridin-2-ols

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Article information

DOI
https://doi.org/10.1039/C2CC35644A
Article type
Communication
Submitted
03 Aug 2012
Accepted
22 Aug 2012
First published
22 Aug 2012

Chem. Commun., 2012,48, 10049-10051

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Enantioselective organocatalytic domino synthesis of tetrahydropyridin-2-ols

J. Wan, C. C. J. Loh, F. Pan and D. Enders, Chem. Commun., 2012, 48, 10049 DOI: 10.1039/C2CC35644A

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