1070872-75-1Relevant articles and documents
Enantiopure quaternary α-trifluoromethyl-α-alkoxyaldehydes from L-tartaric acid derived ketoamides
Nonnenmacher, Jean,Massicot, Fabien,Grellepois, Fabienne,Portella, Charles
, p. 7990 - 7995 (2008/12/22)
(Chemical Equation Presented) 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 K 2CO3 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 α-trifluoromethylated α-alkoxy-aldehydes. This procedure was applied to the preparation of a series of enantiopure aryl, heteroaryl, and alkyl α-trifluoromethyl-α-alkoxyaldehydes.