N-Methylidene[bis(trimethylsilyl)methyl]amine: the first isolable and stable monomeric methanimine allowing thermal [2 + 2] cycloadditions with ketenes

Abstract

N-Methylidene[bis(trimethylsilyl)methyl]amine acts as a stable methanimine synthon [CH₂=NH] equivalent in [2 + 2] cycloadditions to ketenes, generated from acid chlorides and triethylamine, to provide 4-unsubstituted β-lactams in a single step.

References

1. The Chemistry of the Carbon-Nitrogen Double Bond in The Chemistry of Functional Groups, ed. S. Patai, Interscience Publishers, London, 1970.
2. B. Braillon, M. C. Lasne, J. L. Ripoll and J. M. Denis, New J. Chem., 1982, 6, 121; G. A. Harff, A. Sinnema and B. B. Wepster, Recl. Trav. Chim. Pays-Bas, 1979, 98, 71; H. Möhrle, U. Scharf, E. Rühmann and R. Schmid, Arch. Pharm., 1983, 316, 222; M. D. Hurwitz, US Pat. 2 582 128 (Chem. Abstr., 1952, 46, 8146).
3. M. Dal Colle, G. Distefano, D. Jones, A. Guerrino, G. Seconi and A. Modelli, J. Chem. Soc., Perkin Trans. 2, 1994, 789.
4. J. Barluenga, A. M. Bayón and G. Asensio, J. Chem. Soc., Chem. Commun., 1983, 1109; 1984, 427.
5. L. E. Overman and R. M. Burk, Tetrahedron Lett., 1984, 25, 1635.
6. Chemistry and Biology of β-Lactam Antibiotics, ed. R. B. Morin and M. Gorman, Academic, New York, 1982, vols. 1–3; Recent Advances in the Chemistry of β-Lactam Antibiotics, ed. A. G. Brown and S. M. Roberts, The Royal Society of Chemistry, London, 1984; W. Dürckheimer, J. Blumbach, R. Latrell and K. H. Sheunemann, Angew. Chem., Int. Ed. Engl., 1985, 24, 180.
7. A. Capperucci, A. Ricci, G. Seconi, J. Dunogues, S. Grelier, J. P. Picard, C. Palomo and J. M. Aizpurua, J. Organomet. Chem., 1983, 458, C1.
8. J. P. Picard, S. Grelier, T. Constantieux, J. Dunoguès, J. M. Aizpurua, C. Palomo, M. Petraud, B. Barbe, L. Lunnazi and J. M. Leger, Organometallics, 1993, 12, 1378; C. Palomo, J. M. Aizpurua, J. M. Garcia and M. Legido, J. Chem. Soc., Chem. Commun., 1991, 524.
9. O. Nakaguchi, T. Oku, H. Takeno, M. Hashimoto and T. Kamiya, Chem. Pharm. Bull., 1987, 35, 3985.
10. B. Alcaide, L. Casarrubios, G. Dominguez and M. A. Sierra, J. Org. Chem., 1994, 59, 7934; Y. Narukawa, K. N. Juneau, D. Snustad, D. B. Miller and L. S. Hegedus, J. Org. Chem., 1992, 57, 5453; C. Palomo, A. Arrieta, B. Lecea and F. P. Cossio, J. Org. Chem., 1988, 53, 3784; L. E. Overman and T. Osawa, J. Am. Chem. Soc., 1985, 107, 1698.
11. D. A. Evans and E. B. Sjögren, Tetrahedron Lett., 1985, 26, 3783; 3787.
12. J. Lasarte, C. Palomo, J. P. Picard, J. Dunogues and J. M. Aizpurua, J. Chem. Soc., Chem. Commun., 1989, 72.
13. V. Farina, S. I. Hauck and D. Walker, Synlett, 1992, 761; G. I. Georg, P. He, J. Kant and Z. Wu, J. Org. Chem., 1993, 58, 5771.
14. P. G. Mattingly and M. J. Miller, J. Org. Chem., 1980, 45, 410.
15. C. Palomo, J. M. Aizpurua, M. Legido, R. Galarza, P. M. Deya, J. Dunogues, J. P. Picard, A. Ricci and G. Seconi, Angew. Chem., Int. Ed. Engl., 1996, 35, 1239; D. DiPietro, R. M. Borzilleri and S. M. Weinreb, J. Org. Chem., 1994, 59, 5856; G. H. Hakimelahi, M.-J. Shiao, J. R. Hwu and H. Davari, Helv. Chim. Acta, 1992, 75, 1940; B. Alcaide, J. Perez Castells, B. Sanchez Vigo and M. A. Sierra, J. Chem. Soc., Chem. Commun., 1994, 587.