Enantioselective Synthesis of 4-Unsubstituted 3-Alkoxy- and 3-Aminoazetidin-2-ones from Formaldehyde N,N-Dialkylhydrazones
Rosario Fernández Dr.
Dpto. de Química Orgánica Universidad de Sevilla, Seville (Spain)
Search for more papers by this authorAna Ferrete
Dpto. de Química Orgánica Universidad de Sevilla, Seville (Spain)
Search for more papers by this authorJosé M. Lassaletta Dr.
Instituto de Investigaciones Químicas (CSIC-USe) c/ Americo Vespuccio s/n, Isla de la Cartuja 41092 Sevilla (Spain) Fax: (+34) 95-446-0565
Search for more papers by this authorJosé M. Llera Dr.
Dpto. de Química Orgánica y Farmacéutica Universidad de Sevilla 41 081 Sevilla (Spain) Fax: (+34) 954 233 765
Search for more papers by this authorAngeles Monge Dr.
Instituto de Ciencia de Materiales de Madrid, CSIC Madrid (Spain)
Search for more papers by this authorRosario Fernández Dr.
Dpto. de Química Orgánica Universidad de Sevilla, Seville (Spain)
Search for more papers by this authorAna Ferrete
Dpto. de Química Orgánica Universidad de Sevilla, Seville (Spain)
Search for more papers by this authorJosé M. Lassaletta Dr.
Instituto de Investigaciones Químicas (CSIC-USe) c/ Americo Vespuccio s/n, Isla de la Cartuja 41092 Sevilla (Spain) Fax: (+34) 95-446-0565
Search for more papers by this authorJosé M. Llera Dr.
Dpto. de Química Orgánica y Farmacéutica Universidad de Sevilla 41 081 Sevilla (Spain) Fax: (+34) 954 233 765
Search for more papers by this authorAngeles Monge Dr.
Instituto de Ciencia de Materiales de Madrid, CSIC Madrid (Spain)
Search for more papers by this authorWe thank the Dirección General de Investigación Científica y Técnica for financial support (Grant no. PB 97/0747). We also thank the Ministerio de Educación y Ciencia for a doctoral fellowship to A.F.
Abstract
Playing two roles at once, chiral amines from L-proline or D-mannitol act as protecting groups and as chiral auxiliaries in the [2+2] cycloaddition of formaldehyde hydrazones, such as 1, to ketenes. This strategy, based on the stability of the hydrazones as methanimines and on the development of a new oxidative cleavage of hydrazides, provides a short entry to enantiopure 4-unsubstituted 3-alkoxy- and 3-aminoazetidinones with desired configurations. X=OBn, N(CO2Bn)Bn; Bn=benzyl; MMPP=magnesium monoperoxyphthalate.
References
- 1 Reviews:
- 1a R. J. Ternansky, J. M. Morin, Jr. in The Organic Chemistry of β-Lactams ( ), VCH, New York, 1993, p. 257;
- 1b L. Ghosez, J. Marchand-Brynaert in Comprehensive Organic Synthesis, Vol. 5 ( ), Pergamon, Oxford, 1991, p. 85.
- 2 H. Staudinger, Liebigs Ann. Chem. 1907, 356, 51.
- 3 T. Kikuchi, T. Nishinaga, S. Uyeo, O. Yamashiro, K. Minami, Tetrahedron Lett. 1968, 909.
- 4a G. M. Salitura, C. A. Townsend, J. Am. Chem. Soc. 1990, 112, 760;
- 4b C. Cativiela, M. Díaz de Villegas, J. A. Gálvez, Tetrahedron: Asymmetry 1994, 5, 1465.
- 5 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.
- 6a B. Alcaide, A. Rodríguez-Vicente, M. A. Sierra, Tetrahedron Lett. 1998, 39, 163;
- 6b B. Alcaide, L. Casarrubios, G. Domínguez, M. A. Sierra, J. Org. Chem. 1994, 59, 7943;
- 6c B. Alcaide, M. Aly, M. A. Sierra, J. Org. Chem. 1996, 61, 8819;
- 6d S. D. Sharma, U. Mehra, J. P. S. Khurana, S. B. Pandhi, Synthesis 1987, 990;
- 6e A. Arrieta, B. Lecea, F. P. Cossío, C. Palomo, J. Org. Chem. 1987, 53, 3784.
- 7 Selected references:
- 7a J. M. Lassaletta, R. Fernández, Tetrahedron Lett. 1992, 33, 3691;
- 7b D. Enders, R. Syrig, G. Raabe, R. Fernández, C. Gasch, J. M. Lassaletta, J. M. Llera, Synthesis 1996, 48;
- 7c J. M. Lassaletta, R. Fernández, E. Martín-Zamora, E. Díez, J. Am. Chem. Soc. 1996, 118, 7002;
- 7d J. M. Lassaletta, R. Fernández, E. Martín-Zamora, C. Pareja, Tetrahedron Lett. 1996, 37, 5787;
- 7e
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;
10.1002/(SICI)1521-3757(19981217)110:24<3598::AID-ANGE3598>3.0.CO;2-U Web of Science® Google Scholar
- 7f D. Enders, J. Vázquez, G. Raabe, Chem. Commun. 1999, 701.
- 8 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.
- 9 J. K. Whitesell, Chem. Rev. 1989, 89, 1581.
- 10 In contrast with 1 a–e, hydrazone 1 f 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.
- 11 A. Defoin, A. Brouillard-Poichet, J. Streith, Helv. Chim. Acta 1991, 74, 103.
- 12a S. G. Amin, R. D. Glazer, M. S. Manhas, Synthesis 1979, 210;
- 12b G. I. Georg, P. M. Manshava, X. Guan, Tetrahedron Lett. 1991, 32, 581.
- 13 D. A. Evans, E. B. Sjogren, Tetrahedron Lett. 1985, 26, 3783.
- 14 M. J. Burk, J. E. Feaster, J. Am. Chem. Soc. 1992, 114, 6266.
- 15 B. S. Thyagarajan, Mechanism of Molecular Migration, Vol. 2, Wiley, New York, 1967, p. 249.
- 16 The scope and mechanistic aspects of this novel reaction are currently under study in our laboratory.
- 17 Crystal data for (R,S)-3 e: Suitable crystals were obtained from Et2O/cyclohexane at 4 °C. C20H27N3O6, Mr=405.45, crystal size 0.06×0.18×0.20 mm, orthorhombic, space group P212121, a=7.557(2), b=14.066(4), c=19.945(5) Å, V=2120.2(10) Å3, Z=4, ρcalcd=1.270 g cm−3, 2.50°<Θ<20.79°, MoKα radiation (λ=0.71073 Å), T=173(2) K. 3856 reflections collected, 2104 were independent [I>2δ(I)]; 266 parameters, R=0.0774 (wR=0.1291). The crystal was mounted in a CCD diffractometer equipped with a low temperature device and a normal focus, 2.4 kW sealed tube X-ray source operating at 50 kV and 20 mA. Data were collected over a quadrant of the reciprocal space by a combination of two exposure sets, using w scan over the range 3<θ<22°. The intensities were corrected for Lorentz and polarization effects. No absorption correction. The structure was solved by Multan and Fourier methods. Full matrix least-square refinement was carried out minimizing w (F2. Hydrogen atoms were included in their calculated positions. Refinement on F 2 for all reflections. Weighted R factors (wR) and all GOFs are based on F 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: [email protected]).
- 18 (S)-13 had [α]=−19.8 (c=1, CH3OH); D. M. Floyd, A. W. Fritz, J. Pluscec, E. R. Weaver, C. M. Cimarusti, J. Org. Chem. 1982, 47, 5160.
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