N,N-dibenzyloxycarbonylglycyl chloride as useful ketene equivalent in the synthesis of azetidin-2-ones

Synlett

Volumn , Issue 6, 1998, Pages 611-612

  Cainelli, Gianfranco ^a   Galletti, Paola ^a   Giacomini, Daria ^a  

^a UNIVERSITY OF BOLOGNA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000139516     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-1726     Document Type: Article

References (21)

1. Georg, G.I.; Ravikumar, V.T. In The Organic Chemistry of β-Lactams; Georg, G.I., Ed.; VCH Publishers, Inc.: New York, 1993; 295.
2. Georg, G.I. In Studies in Natural Product Chemistry; Rahman, A-ur, Ed.; Elsevier Science: Amsterdam, 1988; vol.2.
3. van der Steen, F.H.; van Koten, G. Tetrahedron 1991, 47, 7503.
4. Hart, D. J.; Ha, D.-C. Chem. Rev. 1989, 89, 1447.
5. Brown, M. J. Heterocycles 1989, 29, 2225.
6. Cainelli, G.; Panunzio, M.; Giacomini, D.; Martelli, G.; Spunta, G.; Bandini, E. In Chemical Synthesis: Gnosis to Prognosis; Chatgilialoglu, C.; Snieckus, V.; Eds NATO ASI 1996.
7. Andreoli, P.; Billi, L.; Cainelli, G.; Panunzio, M.; Bandini, E.; Martelli, G.; Spunta, G. Tetrahedron 1991, 47, 9061.
8. Cainelli, G.; DaCol, M.; Galletti, P.; Giacomini, D. Synlett 1997, 923.
9. Fekner, T.; Baldwin, J. E.; Adlington, R. M.; Schofield, C. J. J. Chem. Soc., Chem .Comm. 1996, 1989.
10. Tsubouchi H.; Tsuji, K.; Ishikawa H. Synlett 1994, 63.
11. N,N-Dibenzyloxycarbonylglycine tert-butyl ester 1 was prepared according to a modified procedure using an excess of NaH instead of KH to prevent the formation of the N,N,N-tribenzyloxycarbonyl amine: Takeuchi, Y.; Nabetani, M.; Takagi, K.; Hagi, T.; Koizumi, T. J. Chem. Soc., Perkin Trans. I 1991, 49
12. Schlessinger, R. H.; Nugent, R.A. J. Am. Chem. Soc. 1982, 104, 1116.
13. The mono N-Cbz glycyl chloride has been previously applied in cycloaddition reactions with acyclic imines but with very low yields (11-22%). See for instance Bose, A.K.; Manhas, M.S.; Chawla, H.P.S.; Dayal, B. J. Chem. Soc., Perkin Trans. I 1975, 1880.
14. 3, 75.5 MHz): 166.1; 153.2; 152.7; 135.8; 134.4; 128.6; 128.5; 128.4; 127.5; 69.6; 68.5; 51.7; 51.6; 45.5; 25.9; 20.8; 17.8; -4.3; -4.6.
15. Kamiya, T.; Hashimoto, M.; Nakaguchi, O.; Oku, T. Tetrahedron 1979, 35, 323.
16. For a recent study on 4-unsubstituted β-lactams see: Palomo, C.; Aizpurua, J.M.; Legido, M.; Galarza, R. J. Chem. Soc., Chem. Comun. 1997, 233.
17. Alcaide, B.; Rodriguez-Vincente, A.; Sierra, M.A. Tetrahedron Lett. 1998, 39, 163.
18. Manhas, M. S.; Amin, S. G.; Ram, B.; Bose, A. K. Synthesis 1976, 689.
19. 4 (2 mmol) and the (2S)-t-butyldimethylsilyloxylactal 9 (1mmol). The resulting mixture was stirred at room temperature until the starting aldehyde was consumed (GC-monitoring). The filtered solution was evaporated to give the crude imine.
20. Cainelli, G.; Panunzio, M.; Bandini, E.; Martelli, G.; Spunta, G. Tetrahedron 1996, 52, 1685.
21. 3, 75.5 MHz): 167.5; 155.7; 136.0; 135.4; 128.8; 128.5; 128.4; 128.1; 127.6; 67.7; 67.2; 61.7; 58.5; 45.7; 25.9; 21.9; 17.9; -3.3; -4.5.