Synthesis and characterization of β-O-Tosyldehydroserine as a precursor of dehydroamino acids

Article abstract of DOI:10.1016/S0040-4039(97)10360-4

β-O-Tosyldehydroserine 3 is prepared directly by the oxidation of the corresponding serine derivative 1 with dimethyl sulfoxide which is activated by p-toluenesulfonyl chloride. The enol tosylate 3 retains reactivities characteristic of aldehydes like those expected for the corresponding dehydroserine derivative 2. A typical reaction of 3 includes substitution of the tosyl group with nucleophiles such as primary and secondary amines, leading to other dehydroamino acids.