One-pot synthesis of trans-β-lactams from ferrocenylketene generated by thermal Wolff rearrangement

References

• (a) Sheehan, J. C. The Enchanted Ring: The Untold Story of Penicillin; MIT: Cambridge, MA, 1982; (b) Brown, K. Penicillin Man: Alexander Fleming and the Antibiotic Revolution; Sutton: London, 2004.
   Google Scholar
• (a) Staudinger, H. Chem. Ber. 1907, 40, 1145–1148; (b) Staudinger, H. Justus Liebigs Ann. Chem. 1907, 356, 51–123.
   Google Scholar
• Georg, G. I.; Ravikumar, V. T. In The Organic Chemistry of β-Lactams; George, G. I., Ed.; VCH: New York, 1993; Chapter 6, pp. 295–368.
   Google Scholar
• (a) For review, see: Fu, N.; Tidwell, T. T. Tetrahedron 2008, 64, 10465–10496; (b) Allen, A. D.; Godoy, J.; Fu, N.; Nagy, M.; Spadaro, S.; Tidwell, T. T.; Vukovic, S. J. Am. Chem. Soc. 2008, 130, 2386–2387.
   Web of Science ®Google Scholar
• (a) Jiao, L.; Liang, Y.; Xu, J. J. Am. Chem. Soc. 2006, 128, 6060–6069; (b) Xu, J. Arkivoc 2009, ix, 21–44; (c) Banik, B. K.; Lecea, B.; Arrieta, A.; de Cózar, A.; Cossío, F. P. Angew. Chem. Int. Ed. 2007, 46, 3028–3032; (d) Cossío, F. P.; Arrieta, A.; Sierra, M. A. Acc. Chem. Res. 2008, 41, 925–936; (e) Palomo, C.; Aizpurua, J. M.; Ganboa, I.; Oiarbide, M. Eur. J. Org. Chem. 1999, 3223–3235; (f) Hu, L.; Wang, Y.; Li, B.; Du, D.-M.; Xu, J. Tetrahedron 2007, 63, 9387–9392.
   PubMed Web of Science ®Google Scholar
• Kagan, H. B.; Luche, J. L. Tetrahedron Lett. 1968, 9, 3093–3096.
   Google Scholar
• von Nussbaum, F.; Brands, M.; Hinzen, B.; Weigand, S.; Habich, D. Angew. Chem. Int. Ed. 2006, 45, 5072–5129.
   PubMed Web of Science ®Google Scholar
• (a) Burnett, D. A.; Caplen, M. A.; Davis Jr, H. R.; Burrier, R. E.; Clader, J. W. J. Med. Chem. 1994, 37, 1733–1736; (b) Rosenblum, S. B.; Huynh, T.; Afonso, A.; Davis Jr, H. R.; Yumibe, N.; Clader, J. W.; Burnett, D. A. J. Med. Chem. 1998, 41, 973–980.
   PubMed Web of Science ®Google Scholar
• Fu, N.-Y.; Yuan, Y.-F.; Pang, M.-L.; Wang, J.-T.; Peppe, C. J. Organomet. Chem. 2003, 672, 52–57.
   Web of Science ®Google Scholar
• van Staveren, D. R.; Metzler-Nolte, N. Chem. Rev. 2004, 104, 5931–5985.
   PubMed Web of Science ®Google Scholar
• (a) Edwards, E. I.; Epton, R.; Marr, G. J. Organomet. Chem. 1975, 85, C23–C25; (b) Edwards, E. I.; Epton, R.; Marr, G. J. Organomet. Chem. 1979, 168, 259–272; (c) Scutaru, D.; Tătaru, L.; Mazilu, I.; Diaconu, E.; Lixandru, T.; Simionescu, Cr. J. Organomet. Chem. 1991, 401, 81–85; (d) Scutaru, D.; Tătaru, L.; Mazilu, I.; Vâtă, M.; Lixandru, T.; Simionescu, Cr. Appl. Organomet. Chem. 1993, 7, 225–231; (e) Sierra, M. A.; Mancheño, M. J.; Vicente, R.; Gómez-Gallego, M. J. Org. Chem. 2001, 66, 8920–8925.
   Web of Science ®Google Scholar
• Bonini, B. F.; Femoni, C.; Comes-Franchini, M.; Fochi, M.; Mazzanti, G.; Ricci, A.; Varchi, G. Synlett 2001, 7, 1092–1096.
   Google Scholar
• (a) Aguilar-Aguilar, A.; Allen, A. D.; Cabrera, E. P.; Fedorov, A.; Fu, N.; Henry-Riyad, H.; Leuninger, J.; Schmid, U.; Tidwell, T. T.; Verma, R. J. Org. Chem. 2005, 70, 9556–9561; (b) Fu, N.; Allen, A. D.; Tidwell, T. T. Arkivoc 2007, iii, 143–150.
   PubMed Web of Science ®Google Scholar
• (a) Li, B.; Wang, Y.; Du, D.-M.; Xu, J. J. Org. Chem. 2007, 72, 990–997; (b) Palomo, C.; Cossio, F. P.; Odriozola, J. M.; Oiarbide, M.; Ontoria, J. M. Tetrahedron Lett. 1989, 30, 4577–4580; (c) Browne, M.; Burnett, D. A.; Caplen, M. A.; Chen, L.-Y.; Clader, J. W.; Domalski, M.; Dugar, S.; Pushpavanam, P.; Sher, R.; Vaccaro, W.; Viziano, M.; Zhao, H. Tetrahedron Lett. 1995, 36, 2555–2558; (d) Hegedus, L. S.; Montgomery, J.; Narukawa, Y.; Snustad, D. C. J. Am. Chem. Soc. 1991, 113, 5784–5791; (e) Arrieta, A.; Cossio, F. P.; Fernandez, I.; Gomez-Gallego, M.; Lecea, B.; Mancheno, M. J.; Sierra, M. A. J. Am. Chem. Soc. 2000, 122, 11509–11510.
   PubMed Web of Science ®Google Scholar
• Banik, B. K.; Becker, F. F. Tetrehedron Lett. 2000, 41, 6551–6554.
   Web of Science ®Google Scholar
• Hansch, C.; Leo, A.; Taft, R. W. Chem. Rev. 1991, 91, 165–195.
   Web of Science ®Google Scholar
• Tidwell, T. T.; Traylor, T. G. J. Am. Chem. Soc. 1966, 88, 3442–3444.
   Web of Science ®Google Scholar
• (a) Allen, A. D.; Colomvakos, J. D.; Diederich, F.; Egle, I.; Hao, X.; Liu, R.; Lusztyk, J.; Ma, J.; McAllister, M. A.; Rubin, Y.; Sung, K.; Tidwell, T. T.; Wagner, B. D. J. Am. Chem. Soc. 1997, 119, 12125–12130; (b) Fu, N.; Allen, A. D.; Kobayashi, S.; Tidwell, T. T.; Vukovic, S. J. Org. Chem. 2008, 73, 1768–1773.
   Web of Science ®Google Scholar
• Georg, G. I.; He, P.; Kant, J.; Wu, Z. J. J. Org. Chem. 1993, 58, 5771–5778.
   Web of Science ®Google Scholar
• (a) Nakajima, T.; Inada, T.; Igarashi, T.; Sekioka, T.; Shimizu, I. Bull. Chem. Soc. Jpn. 2006, 79, 1941–1949; (b) Briquet, A. A. S.; Hansen, H.-J. Helv. Chim. Acta 1994, 77, 1921–1939.
   Web of Science ®Google Scholar
• Further crystallographic data have been deposited with the Cambridge Crystallographic Data Centre. Copies of the data (CCDC 735635) can be obtained free of charge from CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (Tel: +44 1223 762910; Fax: +44 1223 336 033. E-mail: [email protected], http://www.ccdc.cam.ac.uk/deposit).
   Google Scholar