Synfacts 2007(12): 1307-1307  
DOI: 10.1055/s-2007-991323
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Efficient Ruthenium-Catalyzed Oxime-to-Amide Rearrangement

Contributor(s): Paul Knochel, Andrei Gavryushin
N. A. Owston, A. J. Parker, J. M. J. Williams*
University of Bath and AstraZeneca, Bristol, UK
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22. November 2007 (online)


The Beckmann rearrangement of oximes to amides is typically performed under strong acid catalysis. The migration of hydrogen is not common in this reaction. The method developed by the authors gives a simple synthetic pathway from aldehydes to amides, tolerating other functional groups in the molecule. The catalyst loading can be decreased to 0.04 mol% without a significant drop in yield. A broad range of aryl, alkenyl and alkyl aldoximes can be converted ­stereoselectively into the corresponding amides in high yields.