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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 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 [ABSTRACT FROM AUTHOR]

A highly diastereoselective nucleophilic mono(trifluoromethylation) of a tartaric acid-based diketone, using trifluoromethyl(trimethyl)silane, afforded the corresponding γ-keto trifluoromethylcarbinol. The scope and limitation of this reaction was studied. The acidic removal of the acetonide moiety protecting the two hydroxyl groups of the adducts was unsuccessful. Bis(O-methylation) of the aromatic derivatives under basic conditions, followed by acidic hydrolysis and oxidative cleavage, led to two different enantiopure products: an α-aryl-α-methoxy-α-trifluoromethyl ethanal and an α-aryl-α-methoxycarboxylic acid. The overall process is eventually an interesting way to convert one natural chiral raw material into two functionalized enantiopure building blocks including a trifluoromethyl one. [ABSTRACT FROM AUTHOR]

The preparation of aliphatic, aromatic or functionalized tartramides directly from tartaric acid and amines under microwaves activation is described. A preliminary study of the chelating properties of some functionalized tartramides towards Cu2+ ions is reported. To cite this article: R. Plantier-Royon, C. R. Chimie 7 (2004). [Copyright &y& Elsevier]

Abstract: The interactions of three bis(amide) ligands derived from tartaric acid with copper (II) were investigated in aqueous solution by a combination of potentiometry, UV–vis spectrophotometry, electron paramagnetic resonance (EPR), and mass spectrometry. The formation constants of the complexes were measured and their relative structures were reported. The sites of complexation of these ligands are investigated based mostly on their electronic and EPR spectra and on the comparison with the behaviour of some analog compounds. [Copyright &y& Elsevier]