The diastereoselective cyanation of α-keto amides using trimethylsilyl cyanide in the presence of a Lewis acid is described. The corresponding O-acetylated cyanohydrins are obtained in good to high levels of stereoselectivities. The predominance of products with the S absolute configuration at the newly generated stereogenic center was deduced from single crystal X-ray analysis. 13C NMR data suggest that a preferential s-cis conformation was formed by the chelation of a Lewis acid to the dicarbonyl oxygen atoms.
|Number of pages||7|
|Journal||Journal of the Chinese Chemical Society|
|Publication status||Published - 2006 Apr 1|
- Chiral auxiliary
- Lewis acid
- Timethylsilyl cyanide
ASJC Scopus subject areas