Reaction of Organolead Triacetates with 4-Ethoxycarbonyl-2-methyloxazol-5-one. The Synthesis of α-Aryl and α-Vinyl N-Acetylglycine Ethyl Esters and Their Enzymic Resolution.

Article abstract of DOI:10.1016/0040-4039(94)88529-X

An efficient synthesis of the moisture-sensitive compound, 4-ethoxycarbonyl-2-methyloxazol-5-one, has been achieved.This compound undergoes high-yielding arylation and vinylation at the 4-position with organolead triacetates to give compounds which in water are converted to α-aryl and α-vinyl N-acetylglycine ethyl esters.These α-substituted glycine derivatives may be kinetically resolved in very good yield and high enantiomeric excess by enzymic hydrolysis of either the ester group or the amide function of the corresponding carboxylic acids.