Facile transformation of 3,4-disubstituted 2-azetidinones to chiral 5,6-dihydro-2-pyridones

Author:

Lee Hyeon Kyu,Chun Jong Soo,Pak Chwang Siek

Publisher

Elsevier BV

Subject

Organic Chemistry,Drug Discovery,Biochemistry

Reference19 articles.

1. For piperidine and indolizidine alkaloids, see: (a) Elbein, A. D.; Molyneux, R. In Alkaloids; Chemical and Biological Perspectives; Pelletier, S. W., Ed.; John Wiley and Sons: New York, 1987; Vol. 5; (b) Michael, J. P. Nat. Prod. Rep. 1999, 16, 675; (c) O'Hagen, D. Nat. Prod. Rep. 1997, 14, 637; (d) Michael, J. P. Nat. Prod. Rep. 1997, 14, 619.

2. For polyhydroxylated piperidines (azasugars), see: (a) Stutz, A. E. Iminosugars as Glycosidase Inhibiyors; Wiley-VCH: Weinheim, 1998; (b) Sears, P.; Wong, C. H. Angew. Chem., Int. Ed. 1999, 38, 2300; (c) Jacob, G. S. Curr. Opin. Struct. Biol. 1995, 5, 605; (d) Hughes, A. B.; Rudge, A. J. Nat. Prod. Rep. 1994, 11, 135.

3. For some representative examples of previous work, see: (a) Mehta, G.; Mohal, N. Tetrahedron Lett. 2000, 41, 5741; (b) Sun, H.; Millar, K. M.; Yang, J.; Abboud, K.; Horenstein, B. A. Tetrahedron Lett. 2000, 41, 2801; (c) Ma, D.; Sun, H. Org. Lett. 2000, 2, 2503; (d) Yokoyama, H.; Otaya, K.; Kobayashi, H.; Miyazawa, M.; Yamaguchi, S.; Hirai, Y. Org. Lett. 2000, 2, 2427; (e) Davis, F. A.; Chao, B.; Fang, T.; Szewczyk, J. M. Org. Lett. 2000, 2, 1041; (f) Bailey, P. D.; Millwood, P. A.; Smith. P. D. J. Chem. Soc., Chem. Commun. 1998, 633; (g) Yoda, H.; Kawauchi, M.; Takabe, K. Synlett 1998, 137; (h) Goti, A.; Cardona, F.; Brandi, A. Synlett 1996, 761; (i) Toyooka, N.; Yoshida, Y.; Momose, T. Tetrahedron Lett. 1995, 36, 3715; (j) Altenbach, H.-J.; Himmeldirk, K. Tetrahedron: Asymmmetry 1995, 6, 1077; (k) Nukui, S.; Sodeoka, M.; Sasai, H.; Shibasaki, M. J. Org. Chem. 1995, 60, 398; (l) Cook, G. R.; Beholz, L. G.; Stille, J. R. J. Org. Chem. 1994, 59, 3575; (m) Casiraghi, G.; Rassu, G.; Spanu, P.; Pinna, L.; Ulgheri, F. J. Org. Chem. 1993, 58, 3397.

4. For some reviews on β-lactam antibiotics, see: (a) Chemistry and Biology of β-Lactam Antibiotics; Morin, R. B.; Gorman, M., Eds.; Academic Press: New York, 1982; Vol. 1–3; (b) Recent Advances in the Chemistry of β-Lactam Antibiotics; Brown, A. G., Roberts, S. M., Eds.; The Royal Society of Chemistry: Burling House, London, 1984; (c) The Chemistry of β-Lactams; Page, M. I., Ed.; Chapman and Hall: London, 1992.

5. The Organic Chemistry of β-Lactams;Georg,1992

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