Issue 30, 2012
From the journal:

Organic & Biomolecular Chemistry

Efficient proline and prolinol ether mediated 3-component synthesis of 3- and 3,4-substituted chromenone derivatives†

Magnus Rueping,*a   Estíbaliz Merinoa  and  Michael Bolteb  

* Corresponding authors

a RWTH Aachen University, Institute of Organic Chemistry, Landoltweg 1, D-52074 Aachen, Germany
E-mail: magnus.rueping@rwth-aachen.de
Fax: +49 241 8092665

b Department of Inorganic and Analytical Chemistry, Goethe University, Max-von-Laue Strasse 7, 60438 Frankfurt am Main, Germany

Abstract

A highly efficient route for the synthesis of valuable 3,4-substituted chromenone derivatives by the reaction of 1,3-diketones with aldehydes in the presence of L-proline was developed. The reactions take advantage of readily available starting materials and follow a Knoevenagel condensation/Michael addition/hemiacetalization domino process. Chiral 3-substituted chromenones are obtained with high enantioselectivities when a chiral diarylprolinol TMS-ether is applied in the reaction.

Graphical abstract: Efficient proline and prolinol ether mediated 3-component synthesis of 3- and 3,4-substituted chromenone derivatives

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Article information

DOI
https://doi.org/10.1039/C2OB25443C
Article type
Paper
Submitted
29 févr. 2012
Accepted
19 avr. 2012
First published
14 mai 2012

Org. Biomol. Chem., 2012,10, 6201-6210

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Efficient proline and prolinol ether mediated 3-component synthesis of 3- and 3,4-substituted chromenone derivatives

M. Rueping, E. Merino and M. Bolte, Org. Biomol. Chem., 2012, 10, 6201 DOI: 10.1039/C2OB25443C

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