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Synlett 1993; 1993(9): 649-650
DOI: 10.1055/s-1993-22557
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Synthesis of β-Lactams by Means of Sulfur-Controlled Regioselective Radical Cyclizations of N-Ethenyl-α-bromoalkanamides

Hiroyuki Ishibashi* , Chisato Kameoka, Akiko Yoshikawa, Rika Ueda, Kazuya Kodama, Tatsunori Sato, Masazumi Ikeda
  • *Kyoto Pharmaceutical University, Misasagi, Yamashina, Kyoto 607, Japan
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Publication Date:
19 March 2002 (online)

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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