Catalytic nucleophilic glyoxylation of aldehydes.
Beta-silyloxy-alpha-keto esters are prepared through a cyanide-catalyzed benzoin-type reaction with silyl glyoxylates and aldehydes. The products undergo a dynamic kinetic resolution to provide enantioenriched orthogonally protected alcohols and can be converted to the corresponding beta-silyloxy-alpha-amino esters.
Steward
Kimberly M
KM
Department of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599-3290, USA.
Johnson
Jeffrey S
JS
D000447:Aldehydes / Q000737:chemistry*; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D004952:Esters; D006038:Glyoxylates / Q000737:chemistry*; D007659:Ketones / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry; D012821:Silanes / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000447:Aldehydes; D004952:Esters; D006038:Glyoxylates; D007659:Ketones; D009570:Nitriles; D012821:Silanes