Synthesis and Characterization of β‐O‐Tosyldehydroserine as a Precursor of Dehydroamino Acids.

Abstract 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.