Proline-catalysed Mannich reactions of acetaldehyde

Jung Woon Yang, Carley Chandler, Michael Stadler, Daniela Kampen and Benjamin List ()
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Jung Woon Yang: Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, D-45470 Mülheim an der Ruhr, Germany
Carley Chandler: Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, D-45470 Mülheim an der Ruhr, Germany
Michael Stadler: Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, D-45470 Mülheim an der Ruhr, Germany
Daniela Kampen: Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, D-45470 Mülheim an der Ruhr, Germany
Benjamin List: Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, D-45470 Mülheim an der Ruhr, Germany

Nature, 2008, vol. 452, issue 7186, 453-455

Abstract: More Mannich reactions Traditionally, catalysts for organic chemical reactions have been either enzymes or metal complexes. But small organic molecules, known as organocatalysts, have recently burst on to the scene. Organocatalysts are effective in promoting in a wide range of useful transformations, including a carbon–carbon bond forming process known as the Mannich reaction. But frustratingly, these reactions have always failed when the simplest possible substrate, acetaldehyde, was used. Yang et al. have now filled this gap in the organocatalysis spectrum by establishing effective catalytic conditions for Mannich reactions with acetaldehyde. This greatly expands the chemical 'toolkit' of organic chemists, and will be especially useful for making chiral, biologically active compounds.

Date: 2008
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DOI: 10.1038/nature06740

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