We next examined the functional group interconversion chemistry of the malononitrile group (Figure ). Oxidation of the model substrate 3a in presence of base and a nucleophile allowed conversion diastereoselectively to a-hydroxy esters (5a) and amides (5b) with good yields (88% and 61%). a-Hydroxylation was not expected during the oxidation process, which shows the unique electronic properties that the bis-trifluoromethyl groups have on pKa. The stereochemistry of this reaction was determined by Xray crystallography. Reaction with 2-thioaniline yielded benzothiazole with concomitant oxidation as well in 39% yield through a two-step sequence involving amidation and dehydration leading to a bis-trifluoromethylated benzothiazole-piperidine drug-like scaffold. We also investigated select reactivity with the substrate 3b, bearing the more synthetically useful N-Boc protecting group.