Solvent-Free Organocatalytic Michael Reactions

  • Author: Asian Journal of Organic Chemistry
  • Published Date: 26 May 2014
  • Source / Publisher: Asian Journal of Organic Chemistry/Wiley-VCH
  • Copyright: Wiley-VCH Verlag GmbH & Co. KGaA
thumbnail image: Solvent-Free Organocatalytic Michael Reactions

Organocatalysis has become a powerful tool in modern organic synthesis, complementing asymmetric metal-catalyzed and biocatalyzed transformations. It has led to the development of new convenient strategies to synthesize a variety of chiral building blocks.

As part of their project on the development of more sustainable organocatalytic procedures, Eusebio Juaristi and co-workers, Centro de Investigación y de Estudios Avanzados del Instituto Politénico Nacional (CINVESTAV), Mexico City, Mexico, have explored the use of mechanochemical energy under solvent-free reaction conditions. In this context, they have reported a convenient synthetic procedure for the preparation of chiral thiohydantoins (pictured) by coupling a protected L-proline derivative with isothiocyanates derived from a number of natural α-amino acids.

These chiral heterocycles were tested as organocatalysts in the asymmetric Michael addition reaction. The reactions of interest proceeded with high diastereo- and enantioselectivity, with various Michael acceptors and under solvent-free conditions.
Such reactions could provide a key method for decreasing the environmental impact of such chemical transformations.

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Magazine of Chemistry Europe (16 European Chemical Societies)published by Wiley-VCH