Ruthenium Catalyzed Oxidation of 3-Amino-β-Lactams

Synlett

Volumn 1997, Issue 8, 1997, Pages 923-924

  Cainelli, Gianfranco ^a   DaCol, Marco ^b   Galletti, Paola ^a   Giacomini, Daria ^a  

^a UNIVERSITY OF BOLOGNA   (Italy)

^b Biochimica OPOS SpA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0010324784     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-941     Document Type: Article

References (15)

1. Wild, H. In The Organic Chemistry of β-lactams; Georg, G.I., Ed.; VCH, 1993.
2. Wickel, S. Aldrichimica Acta 1985, 18, 95. Nagahara, T.; Kametani, T. Heterocycles 1987, 25, 729.
3. Wickel, S. Aldrichimica Acta 1985, 18, 95. Nagahara, T.; Kametani, T. Heterocycles 1987, 25, 729.
4. Suarato, A.; Lombardi, P.; Galliani, C.; Franceschi, G. Tetrahedron Lett. 1978, 4059.
5. Andreoli, P.; Billi, L.; Cainelli, G.; Panunzio, M.; Bandini, E.; Martelli, G.; Spunta, G. Tetrahedron 1991, 47, 9061.
6. Murahashi, S-I.; Saito, T.; Naota, T.; Kumobayashi, H.; Akutagawa, S. Tetrahedron Lett. 1991, 32, 2145.
7. Murahashi, S-I.; Naota, T.; Kuwabara, T.; Saito, T.; Kumobayashi, H.I.; Akutagawa, S. J. Am. Chem. Soc. 1990, 112, 7820.
8. To our knowledge, the only example reported in the literature concerns to the oxidation of 5a to give the corresponding 4-acetyloxy and benzoyloxy derivative: Easton, C. J.; Love, S.G.; Wang, P. J. Chem. Soc. Perkin Trans. 1 1990, 277.
9. Kamiya, T.; Hashimoto, M.; Nakaguchi, O.; Oku, T. Tetrahedron 1979, 35, 323.
10. 2, 0°C, 1 min) (cfr. J. Am. Chem. Soc. 1982, 104, 1116).
11. 2, 0°C, 1 min) (cfr. J. Am. Chem. Soc. 1982, 104, 1116).
12. 13C NMR, IR).
13. 2 (3x15mL). The organic solution was washed with 10% aqueous solution of sodium sulfite (20mL), with brine and dried over sodium sulfate. Evaporation followed by column chromatography on silica gel (cyclohexane/ethyl acetate=6/4) gave 6a (177 mg, 0.65 mmol, 65%) in a 13/87 cis/trans ratio.
14. 2/EtOH, refunctionalization as 3-phenylacetamido-azetidin-2-one under Schotten-Baumann conditions, protection of the amidic hydrogen with NaH/CbzCl in THF and final deprotection of the N-allyl group.
15. Murahashi, S-I., Angew. Chem. Int. Ed. Engl. 1995, 34, 2443.