New synthesis of penems via a reductive cyclization reaction of oxalimides with trialkyl phosphite.
1983; Pharmaceutical Society of Japan; Volume: 31; Issue: 2 Linguagem: Inglês
10.1248/cpb.31.768
ISSN1347-5223
AutoresAkira Yoshida, Teruo Hayashi, Noriko Takeda, S. OIDA, Eiji Ohki,
Tópico(s)Synthetic Organic Chemistry Methods
ResumoTreatment of the oxalimide 5 with triethyl phosphite formed the penem 3 and the triethoxyphosphonium ylide 7, presumably via the common carbene intermediate 10. Prolonged heating of 7 afforded 3 and its C-5 epimer. Similar reaction of the oxalimide 13 with trimethyl phosphite gave only the ylide 14, which was further heated to cyclize to the penem 15.
Referência(s)