Use of lithium (α-methylbenzyl)allylamide for a formal asymmetric synthesis of thienamycin

Abstract

The highly stereoselective conjugate addition of lithium (αR)-(α-methylbenzyl)allylamide 3 to (E)-tert-butyl penta-2,4-dienoate 4, followed by a stereoselective aldol reaction with acetaldehyde, are the key steps in the synthesis of the known β-lactam intermediate, (3S,4R)-3-[(R)-1-(tert-butyldimethyls ilyloxy)ethyl]-4-vinylazetidin-2-one 2, for elaboration to thienamycin and its derivatives.

References

1. H. Kropp, J. S. Kahan, F. M. Kahan, J. Sanderof, G. Darland and J. Birnbaum, Abstract 228, 16th Intersci. Conf. Antimicrob. Agents and Chemother., Chicago 1976; J. S. Kahan, F. M. Kahan, R. Goegelman, S. A. Currie, M. Jackson, E. O. Stapley, T. W. Miller, A. K. Miller, D. Hendlin, S. Mochales, S. Hernandez, H. B. Woodruff and J. Birnbaum, J. Antibiot., 1979, 32, 1; G. Albers-Schönberg, B. H. Arison, O. D. Hensens, J. Hirshfield, K. Hoogsteen, E. A. Kaczka, R. E. Rhodes, J. S. Kahan, F. M. Kahan, R. W. Ratcliffe, E. Walton, L. J. Ruswinkle, R. B. Morin and B. G. Christensen, J. Am. Chem. Soc., 1978, 100, 6491.
2. For reviews, see: R. C. Thomas, in Recent Progress in the Chemical Synthesis of Antibiotics, ed. G. Lukacs and M. Ohno, Springer-Verlag, Berlin, 1990; R. J. Ternansky and J. M. Morin Jr., in The Organic Chemistry of β-Lactams, ed. G. I. Georg, VCH, New York, 1993.
3. D. H. Shih, F. Baker, L. Cama and B. G. Christensen, Heterocycles, 1984, 21, 29; D. R. Bender, A. M. DeMarco, D. G. Melillo, S. M. Riseman and I. Shinkai, J. Org. Chem., 1992, 57, 2411.
4. C. Bismara, R. Di Fabio, d. Donati, T. Rossi and R. J. Thomas, Tetrahedron Lett., 1995, 36, 4283 and references cited therein.
5. Y. Yamamoto, N. Asao and T. Uyehara, J. Am. Chem. Soc., 1992, 114, 5427.
6. S. G. Davies and O. Ichihara, Tetrahedron: Asymmetry, 1991, 2, 183.
7. N. Asao, N. Tsukada and Y. Yamamoto, J. Chem. Soc., Chem. Commun., 1993, 1660.
8. S. G. Davies and D. R. Fenwick, J. Chem. Soc., Chem. Commun., 1995, 1109.
9. S. G. Davies, C. J. R. Hedgecock and J. M. McKenna, Tetrahedron: Asymmetry, 1995, 6, 827; 1995, 6, 2507.
10. K. Hattori, M. Miyata and H. Yamamoto, J. Am. Chem. Soc., 1993, 115, 1151.
11. Y. Ito, Y. Kobayashi, T. Kawabata, M. Takase and S. Terashima, Tetrahedron, 1989, 45, 5767.
12. F. Garro-Helion, A. Merzouk and F. Guibé, J. Org. Chem., 1993, 58, 6109.
13. S. Kobayashi, T. Iimori, T. Izawa and M. Ohno, J. Am. Chem. Soc., 1981, 103, 2406.
14. S. T. Hodgson, D. M. Hollinshead and S. V. Ley, Tetrahedron, 1985, 41, 5871.