Radical reaction of Williams’ glycinate auxiliaries with α-amidoacrylates: synthesis of orthogonally functionalized (2R,4R)- and (2R,4S)-diaminoglutamic acids

Orthogonally functionalized (2R,4S)- and (2R,4R)-diaminoglutamic acids 10, 11, and 12, 13 were obtained in three steps starting from (2S,3R)-(+)-6-oxo-2,3-diphenyl-4-morpholinecarboxylate 5, employing a radical reaction of selenide 6 with methyl 2-acetamidoacrylate 7 as a key step.