Reductive alkylation of active methylene compounds with carbonyl derivatives, calcium hydride and a heterogeneous catalyst

Carole Guyon; Marie-Christine Duclos; Marc Sutter; Estelle Métay; Marc Lemaire

doi:10.1039/C5OB00849B

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Reductive alkylation of active methylene compounds with carbonyl derivatives, calcium hydride and a heterogeneous catalyst†

Carole Guyon,^a Marie-Christine Duclos,^a Marc Sutter,^a Estelle Métay*^a and Marc Lemaire*^a

Author affiliations

* Corresponding authors

^a Equipe Catalyse Synthèse Environnement, Institut de Chimie et Biochimie Moléculaires et Supramoléculaires, UMR-CNRS 5246, Université de Lyon, Université Claude Bernard-Lyon 1, Bâtiment Curien, 43 boulevard du 11 Novembre 1918, F-69622 Villeurbanne Cedex, France
E-mail: estelle.metay@univ-lyon1.fr
Fax: +33 (0)4 72 43 14 08
Tel: +33 (0)4 72 44 85 07

Abstract

A one-pot two-step reaction (Knoevenagel condensation – reduction of the double bond) has been developed using calcium hydride as a reductant in the presence of a supported noble metal catalyst. The reaction between carbonyl compounds and active methylene compounds such as methylcyanoacetate, 1,3-dimethylbarbituric acid, dimedone and the more challenging dimethylmalonate, affords the corresponding monoalkylated products in moderate to good yields (up to 83%) with minimal reduction of the starting carbonyl compounds.

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Article information

DOI: https://doi.org/10.1039/C5OB00849B
Article type: Paper
Submitted: 27 Apr 2015
Accepted: 29 May 2015
First published: 29 May 2015

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Org. Biomol. Chem., 2015,13, 7067-7075

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Reductive alkylation of active methylene compounds with carbonyl derivatives, calcium hydride and a heterogeneous catalyst

C. Guyon, M. Duclos, M. Sutter, E. Métay and M. Lemaire, Org. Biomol. Chem., 2015, 13, 7067 DOI: 10.1039/C5OB00849B

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Organic & Biomolecular Chemistry

Reductive alkylation of active methylene compounds with carbonyl derivatives, calcium hydride and a heterogeneous catalyst†

Abstract

Supplementary files

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Reductive alkylation of active methylene compounds with carbonyl derivatives, calcium hydride and a heterogeneous catalyst

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