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Synfacts 2011(1): 0052-0052  
DOI: 10.1055/s-0030-1259172
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Magnesium-Promoted N-Selective Alkylation of Amides and Carbamates

Contributor(s): Mark Lautens, Jane Panteleev
Y.-Q. Fang*, M. M. Bio*, K. B. Hansen, M. S. Potter, A. Clausen
Amgen Inc., Cambridge, USA
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Publication History

Publication Date:
21 December 2010 (online)

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Significance

The authors describe a stereospecific N-alkylation of 2-pyridones, amides, and ­carbamates with chiral α-halocarboxylic acids 2. ­Stereospecific addition of oxygen nucleophiles to 2 are known, but secondary amide nucleophiles pose a bigger challenge in this reaction because of undesired competitive O-alkylation and base-promoted substrate or product racemization.