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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)


Abstract

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



Lanthanum Tricyanide-Catalyzed Acyl Silane-Ketone Benzoin Additions

J. C. Tarr, J. S. Johnson, Org. Lett., 2009, 11, 3870-3873.


Key Words

α-hydroxy carbonyl compounds


ID: J54-Y2010-1750