Stereoselective Synthesis of Aminoalkyl-Substituted β-Lactams via Cycloaddition of Ketenes Generated from α-Amino Acids

Synlett

Volumn 1996, Issue 6, 1996, Pages 582-584

  Podlech, Joachim ^a  

^a UNIVERSITY OF STUTTGART   (Germany)

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[No Author keywords available]

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EID: 0002986336     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5469     Document Type: Article

References (28)

1. Arndt, F.; Eistert, B.; Partale, W. Ber. Dtsch. Chem. Ges. 1927, 60, 1364. Ye, T.; McKervey, M. A. Chem. Rev. 1994, 94, 1091.
2. Arndt, F.; Eistert, B.; Partale, W. Ber. Dtsch. Chem. Ges. 1927, 60, 1364. Ye, T.; McKervey, M. A. Chem. Rev. 1994, 94, 1091.
3. Balenović, K.; Jambrešić, I.; Gašpert, B.; Cerar, D. Recl. Trav. Chim. Pays-Bas 1956, 75, 1252. Balenović, K.; Štimac, N. Croat. Chem. Acta 1957, 29, 153 and references cited therein.
4. Balenović, K.; Jambrešić, I.; Gašpert, B.; Cerar, D. Recl. Trav. Chim. Pays-Bas 1956, 75, 1252. Balenović, K.; Štimac, N. Croat. Chem. Acta 1957, 29, 153 and references cited therein.
5. inter alia: Jefford, C. W.; Tang, Q.; Zaslona, A.; J. Am. Chem. Soc. 1991, 113, 3513. Evans, D. A.; Miller, S. J. Ennis, M. D.; J. Org. Chem. 1993, 58, 471.
6. inter alia: Jefford, C. W.; Tang, Q.; Zaslona, A.; J. Am. Chem. Soc. 1991, 113, 3513. Evans, D. A.; Miller, S. J. Ennis, M. D.; J. Org. Chem. 1993, 58, 471.
7. Podlech, J; Seebach, D. Liebigs Ann. Chem. 1995, 1217.
8. Podlech, J; Seebach, D. Angew. Chem. 1995, 107, 507; Angew. Chem. Int. Ed. Engl. 1995, 34, 471.
9. Podlech, J; Seebach, D. Angew. Chem. 1995, 107, 507; Angew. Chem. Int. Ed. Engl. 1995, 34, 471.
10. Guibourdenche, C.; Podlech, J.; Seebach, D. in preparation for Liebigs Ann. Chem.
11. Some examples of cycloadditions with ketenes generated from achiral substrates are reviewed in: Backes, J. In Houben-Weyl, 4th. ed., Voll. E16b; Klamann, D., Ed.; Thieme: Stuttgart, 1991; p. 460.
12. Aminoalkyl-substituted β-lactams have been recently prepared by reaction of the ester enolates of methyl 3-(dialkylamino)-butanoates with various imines. This led to mixtures of up to four diastereoisomeric β-lactams: Alcaide, B.; Esteban, G.; Martín-Cantalejo, Y.; Plumet, J.; Rodríguez-López, J.; Monge, A.; Pérez-García, V. J. Org. Chem. 1994, 59, 7994.
13. The Chemistry of β-Lactams; Page, M. I., Ed.; Blackie Academic & Professional: London, 1992.
14. When the diazoketones were reacted with silver benzoate in the presence of imine 9, no reaction occurred and the diazoketone was recovered quantitatively.
15. The diazoketones were prepared in accordance with the procedures described in the literature: Podlech, J.; Seebach, D. Helv. Chim. Acta 1995, 78, 1238; and lit. 4.
16. We examined the influence of the amount of imine (1.1 to 4 eq.) in this reaction and found no significant difference in the yields.
17. Compound 9 was prepared in accordance to Juday, R.: Adkins. H. J. Am. Chem. Soc. 1955, 77, 4559. For the preparation of 18 and 19 see: Texier-Boullet, F. Synthesis, 1985, 679.
18. Compound 9 was prepared in accordance to Juday, R.: Adkins. H. J. Am. Chem. Soc. 1955, 77, 4559. For the preparation of 18 and 19 see: Texier-Boullet, F. Synthesis, 1985, 679.
19. The relative configurations of the β-lactams given in Scheme 2 were proved by X-ray crystallographic examination of 11a and 12a. Comparison of the NMR spectroscopic data allowed the assignment of the configuration in the other compounds.
20. 3; C, 76.29; H, 7.06; N, 6.14. Found; C, 76.13; H, 7.15; N, 5.90.
21. 20 and elemental analysis).
22. Nevertheless, due to intramolecular proton migrations, the phthaloyl protection is often unsuitable when the decomposition of the diazoketone is induced photochemically. The lower yield in the preparation of 12a,b might be caused by this effect: Griesbeck, A.; Henz, A.; Peters, K.; Peters, E.-M.; von Schnering, H. G. Angew. Chem. 1995, 107, 498; Angew. Chem. Int. Ed. Engl. 1995, 34, 474. Griesbeck, A. G.; Mauder, H. Angew. Chem. 1992, 104, 97; Angew. Chem. Int. Ed. Engl. 1992, 31, 73.
23. Nevertheless, due to intramolecular proton migrations, the phthaloyl protection is often unsuitable when the decomposition of the diazoketone is induced photochemically. The lower yield in the preparation of 12a,b might be caused by this effect: Griesbeck, A.; Henz, A.; Peters, K.; Peters, E.-M.; von Schnering, H. G. Angew. Chem. 1995, 107, 498; Angew. Chem. Int. Ed. Engl. 1995, 34, 474. Griesbeck, A. G.; Mauder, H. Angew. Chem. 1992, 104, 97; Angew. Chem. Int. Ed. Engl. 1992, 31, 73.
24. Nevertheless, due to intramolecular proton migrations, the phthaloyl protection is often unsuitable when the decomposition of the diazoketone is induced photochemically. The lower yield in the preparation of 12a,b might be caused by this effect: Griesbeck, A.; Henz, A.; Peters, K.; Peters, E.-M.; von Schnering, H. G. Angew. Chem. 1995, 107, 498; Angew. Chem. Int. Ed. Engl. 1995, 34, 474. Griesbeck, A. G.; Mauder, H. Angew. Chem. 1992, 104, 97; Angew. Chem. Int. Ed. Engl. 1992, 31, 73.
25. Nevertheless, due to intramolecular proton migrations, the phthaloyl protection is often unsuitable when the decomposition of the diazoketone is induced photochemically. The lower yield in the preparation of 12a,b might be caused by this effect: Griesbeck, A.; Henz, A.; Peters, K.; Peters, E.-M.; von Schnering, H. G. Angew. Chem. 1995, 107, 498; Angew. Chem. Int. Ed. Engl. 1995, 34, 474. Griesbeck, A. G.; Mauder, H. Angew. Chem. 1992, 104, 97; Angew. Chem. Int. Ed. Engl. 1992, 31, 73.
26. In one experiment, we tested the effect of the addition of 3 eq. LiCl on the transformation 2 → 11a,b. While the product ratio did not change, the yield rose to 81 %.
27. Georg, G. I.; Ravikumar, V. T. In The Organic Chemistry of β-Lactams; Georg, G. I., Ed.; VCH: New York, 1993; p 295.
28. An intramolecular stabilization of the ketene through nucleophilic attack of the carbonyl group present in the protection group at the nitrogen 5 seems to play no important role in the mechanism. Although there is no carbonyl group in 1-diazohexan-2-one, which could result in such a stabilization, this molecule also leads to a trans-substituted β-lactam when photochemically decomposed in the presence of imine 9.