Enantiopure quaternary alpha-trifluoromethyl-alpha-alkoxyaldehydes from L-tartaric acid derived ketoamides.
The diastereoselective nucleophilic trifluoromethylation of a range of ketoamides derived from L-tartaric acid has been studied. TMSCF3 in the presence of a catalytic amount of K2CO3 in DMF has been identified as the conditions leading to the highest diastereoselectivities. A sequential one-pot reaction trifluoromethylation-etherification of the trifluoromethylcarbinol has been developed. Only one further one-pot reaction, ketal hydrolysis-oxidative cleavage, led to the final alpha-trifluoromethylated alpha-alkoxyaldehydes. This procedure was applied to the preparation of a series of enantiopure aryl, heteroaryl, and alkyl alpha-trifluoromethyl-alpha-alkoxyaldehydes.
Nonnenmacher
Jean
J
Université de Reims Champagne-Ardenne, Institut de Chimie Moléculaire de Reims, CNRS UMR 6229, UFR des Sciences Exactes et Naturelles, BP 1039, 51687 Reims Cedex 2, France.
Massicot
Fabien
F
Grellepois
Fabienne
F
Portella
Charles
C
D000447:Aldehydes / Q000138:chemical synthesis / Q000737:chemistry*; D000478:Alkylation; D000577:Amides / Q000737:chemistry*; D002384:Catalysis; D004126:Dimethylformamide / Q000737:chemistry; D006845:Hydrocarbons, Fluorinated / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D012821:Silanes / Q000737:chemistry*; D013237:Stereoisomerism; D013644:Tartrates / Q000737:chemistry*
D000447:Aldehydes; D000577:Amides; D006845:Hydrocarbons, Fluorinated; D007659:Ketones; D012821:Silanes; D013644:Tartrates; D004126:Dimethylformamide; C509472:trimethyl(trifluoromethyl)silane; C029768:tartaric acid