摘要

The diastereoselective cyanation of alpha-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. C-13 NMR data suggest that a preferential s-cis conformation was formed by the chelation of a Lewis acid to the dicarbonyl oxygen atoms.

  • 出版日期2006-4