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Synfacts 2008(1): 0058-0058  
DOI: 10.1055/s-2007-991431
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Asymmetric Metallophosphite-Induced C-Acylation of Nitrones

Contributor(s): Hisashi Yamamoto, Joshua N. Payette
M. R. Garrett, J. C. Tarr, J. S. Johnson*
University of North Carolina at Chapel Hill, USA
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Publication History

Publication Date:
18 December 2007 (online)

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Significance

The authors have previously reported the use of metallophosphites as Umpolung catalysts for the C-acylation of aldehydes and alkenes. The present study reports the first examples of direct C-acylation of nitrones. Reactions of electron-neutral or electron-rich acyl silanes with electronically diverse N-aryl nitrones were well tolerated providing products in high yields and ee values. Further, the product N-O bond is reductively cleaved using Zn metal to reveal the enantio-enriched N-aryl α-amino ketone.