Synthesis of Amino-β-lactams by the Photolytic Reaction of Imines with Pentacarbonylchromium(0)

Article abstract of DOI:10.1021/ja00238a018

Chromium-carbene complexes containing the <=C(H)NR2> group were synthesized by the reaction of Vilsmeir's salts with Cr(CO)5^2-.These carbenes were remarkably air stable and resistant to attack by nucleophiles.Photolytic reaction of these complexes with imines, oxazines, oxazolines, imidates, thiazines, and thiazolines produced β-lactams in fair to good yield.In most cases trans stereochemistry was observed.Representative dibenzylamino-β-lacatms were debenzylated to produce β-lactams having a free NH2 group α to the lactam carbonyl group.