Catalytic Nucleophilic Glyoxylation of Aldehydes
Kimberly M. Steward and Jeffrey S. Johnson*
*Department of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599-3290, Email: jsjunc.edu
K. M. Steward, J. S. Johnson, Org. Lett., 2010, 12, 2864-2867.
DOI: 10.1021/ol100996w (free Supporting Information)
β-Silyloxy-α-keto esters are prepared through a cyanide-catalyzed benzoin-type reaction with silyl glyoxylates and aldehydes. A subsequent dynamic kinetic resolution provides enantioenriched orthogonally protected alcohols, that can be converted to the corresponding β-silyloxy-α-amino esters.
see article for more examples
J. C. Tarr, J. S. Johnson, Org. Lett., 2009, 11, 3870-3873.