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Updated: May 22, 2025

A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis
Published on: February 16, 2020
Organocatalytic kinetic resolution of 1,5-dicarbonyl compounds through a retro-Michael reaction
James Guevara-Pulido1, Fernando González-Pérez2, José M Andrés2
1Química Farmacéutica, Grupo Investigación en Química Aplicada INQA, Universidad El Bosque, Cra 7b Bis No 132 - 11, Bogotá, Colombia.
Abstract:
The pharmaceutical chemical industry has long used kinetic resolution to obtain high-value compounds. Organocatalysis has recently been added to this strategy, allowing for the resolution of racemic mixtures with low catalyst loadings and mild reaction conditions. This research focuses on the kinetic resolution of 1,5-dicarbonyl compounds using a retro-Michael reaction, co-catalyzed at room temperature with 20 mol % of the Jørgensen-Hayashi catalyst and PNBA. The study highlights the importance of conducting the kinetic resolution at a concentration of approximately ten millimolar (mM) to prevent the Michael retro-Michael equilibrium from affecting the process.
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In the first step, as depicted in Figure 1, the base deprotonates the β-hydroxy ketone at the hydroxyl group to form an alkoxide ion.

