Enantioselective synthesis of 4-unsubstituted 3-alkoxy- and 3-aminoazetidin-2-ones from formaldehyde N,N-dialkylhydrazones

Angewandte Chemie - International Edition

Volumn 39, Issue 16, 2000, Pages 2893-2897

  Fernández, Rosario ^b   Ferrete, Ana ^b   Lassaletta, José M ^a   Llera, José M ^b   Monge, Angeles ^c  

^a INSTITUTO DE INVESTIGACIONES QUÍMICAS   (Spain)

^b UNIVERSITY OF SEVILLE   (Spain)

^c INSTITUTO DE CIENCIA DE MATERIALES DE MADRID   (Spain)

Author keywords

Asymmetric synthesis; Cycloadditions; Hydrazones; Ketenes; Lactams

Indexed keywords

AZETIDINE DERIVATIVE; FORMALDEHYDE; HYDRAZONE DERIVATIVE; KETENE DERIVATIVE; LACTAM;

ARTICLE; CHEMICAL BOND; CHROMATOGRAPHY; CRYSTAL STRUCTURE; CYCLIZATION; DIASTEREOISOMER; OXIDATION; SYNTHESIS; THERMOSTABILITY; X RAY DIFFRACTION;

EID: 0039592749     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3773(20000818)39:16<2893::AID-ANIE2893>3.0.CO;2-E     Document Type: Article

References (33)

1. Reviews: a) R. J. Ternansky, J. M. Morin, Jr. in The Organic Chemistry of β-Lactams (Ed.: G. I. Georg). VCH, New York, 1993, p. 257;
2. b) L. Ghosez, J. Marchand-Brynaert in Comprehensive Organic Synthesis, Vol. 5 (Eds.: B. Trost, I. Fleming), Pergamon, Oxford, 1991, p. 85.
3. H. Staudinger, Liebigs Ann. Chem. 1907, 356, 51.
4. T. Kikuchi, T. Nishinaga, S. Uyeo, O. Yamashiro, K. Minami, Tetrahedron Lett. 1968, 909.
5. a) G. M. Salitura, C. A. Townsend, J. Am. Chem. Soc. 1990, 112, 760;
6. b) C. Cativicla, M. Díaz de Villegas, J. A. Gálvez, Tetrahedron: Asymmetry 1994, 5, 1465.
7. As a remarkable exception, N-methylene[bis(trimethylsilyl)methyl]-amine has recently been described as a stable, monomeric compound suitable for cycloaddition reactions with ketenes: C. Palomo, J. M. Aizpurua, M. Legido, R. Lagarza, Chem. Commun. 1997, 233.
8. a) B. Alcaide, A. Rodríguez-Vicente, M. A. Sierra, Tetrahedron Lett. 1998, 39, 163;
9. b) B. Alcaide, L. Casarrubios, G. Domínguez, M. A. Sierra, J. Org. Chem. 1994, 59, 7943;
10. B. Alcaide, M. Aly, M. A. Sierra, J. Org. Chem. 1996, 61, 8819;
11. S. D. Sharma, U. Mehra, J. P. S. Khurana, S. B. Pandhi, Synthesis 1987, 990;
12. e) A. Arrieta, B. Lecea, F. P. Cossío, C. Palomo, J. Org. Chem. 1987, 53, 3784.
13. Selected references: a) J. M. Lassaletta, R. Fernández, Tetrahedron Lett. 1992, 33, 3691;
14. b) D. Enders, R. Syrig, G. Raabe, R. Fernández, C. Gasch, J. M. Lassaletta, J. M. Llera, Synthesis 1996, 48;
15. J. M. Lassaletta, R. Fernández, E. Martín-Zamora, E. Díez, J. Am. Chem. Soc. 1996, 118, 7002;
16. J. M. Lassaletta, R. Fernández, E. Martín-Zamora, C. Pareja, Tetrahedron Lett. 1996, 37, 5787;
17. e) R. Fernández, E. Martín, C. Pareja, J. Vázquez, E. Díez, A. Monge, J. M. Lassaletta, Angew. Chem. 1998, 110, 3598; Angew. Chem. Int. Ed. 1998, 37, 3428;
18. e) R. Fernández, E. Martín, C. Pareja, J. Vázquez, E. Díez, A. Monge, J. M. Lassaletta, Angew. Chem. 1998, 110, 3598; Angew. Chem. Int. Ed. 1998, 37, 3428;
19. f) D. Enders, J. Vázquez, G. Raabe, Chem. Commun. 1999, 701.
20. The cycloaddition reaction of phenoxyketene with ketone hydrazones to give racemic 1-amino β-lactams has been reported. Surprisingly, no yields were included: S. D. Sharma, S. B. Pandhi, J. Org. Chem. 1990, 55, 2196.
21. J. K. Whitesell, Chem. Rev. 1989, 89, 1581.
22. In contrast with 1a-e, hydrazone 1f failed in the 1,2 addition to trifluoromethyl ketones: C. Pareja, E. Martín-Zamora, R. Fernández, J. M. Lassaletta, J. Org. Chem. 1999, 64, 8846. In addition, ab initio calculations predict an almost perfect planar geometry for the hydrazone moiety in the transition states corresponding to the addition of N,N-dialkylhydrazones to π-electrophiles: R. R. Pappalardo, J. M. Muñoz, R. Fernández, J. M. Lassaletta, unpublished results.
23. In contrast with 1a-e, hydrazone 1f failed in the 1,2 addition to trifluoromethyl ketones: C. Pareja, E. Martín-Zamora, R. Fernández, J. M. Lassaletta, J. Org. Chem. 1999, 64, 8846. In addition, ab initio calculations predict an almost perfect planar geometry for the hydrazone moiety in the transition states corresponding to the addition of N,N-dialkylhydrazones to π-electrophiles: R. R. Pappalardo, J. M. Muñoz, R. Fernández, J. M. Lassaletta, unpublished results.
24. A. Defoin, A. Brouillard-Poichet, J. Streith, Helv. Chim. Acta 1991, 74, 103.
25. a) S. G. Amin, R. D. Glazer, M. S. Manhas, Synthesis 1979, 210;
26. b) G. I. Georg, P. M. Manshava, X. Guan, Tetrahedron Lett. 1991, 32, 581.
27. D. A. Evans, E. B. Sjogren, Tetrahedron Lett. 1985, 26, 3783.
28. M. J. Burk, J. E. Feaster, J. Am. Chem. Soc. 1992, 114, 6266.
29. B. S. Thyagarajan, Mechanism of Molecular Migration, Vol. 2, Wiley, New York, 1967, p. 249.
30. The scope and mechanistic aspects of this novel reaction are currently under study in our laboratory.
31. 2; conventional R factors are based on F. The configuration of C-3 is based on that known for C-2′ in the auxiliary. Crystallographic data (excluding structure factors) for the structure reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-135522. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax: (+ 44) 1223-336-033; e-mail: deposit@ccdc.cam.ac.uk).
32. 3OH); D. M. Floyd, A. W. Fritz, J. Pluscec, E. R. Weaver, C. M. Cimarusti, J. Org. Chem. 1982, 47, 5160.
33. 3OH); D. M. Floyd, A. W. Fritz, J. Pluscec, E. R. Weaver, C. M. Cimarusti, J. Org. Chem. 1982, 47, 5160.