Synthesis of β-Lactams by Means of Sulfur-Controlled Regioselective Radical Cyclizations ofN-Ethenyl-α-bromoalkanamides

Abstract
N-[2-Phenylthio- or 2,2-bis(phenylthio)ethenyl]-α-bromoalkanamides 5, upon treatment with Bu3SnH in the presence of AIBN, undergo radical cyclization in a 4-exo-trig manner to give β-lactams 6. Similar treatment of enamide 11b, prepared from L-threonine, afforded two diastereoisomers 12b and 13b in a ratio of ca. 2 : 1

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