On the question of the diastereoselective alkylation of 4-unsubstituted 3-amino β-lactams. A concise synthesis of α-branched α-amino β-lactams and their coupling with α-amino acid esters

Tetrahedron

Volumn 56, Issue 31, 2000, Pages 5563-5570

  Palomo, Claudio ^a   Aizpurua, Jesus M ^a   Galarza, Regina ^a   Benito, Ana ^a   Khamrai, Uttam K ^a   Eikeseth, Unni ^a   Linden, Anthony ^b  

^a UNIVERSITY OF THE BASQUE COUNTRY UPV EHU   (Spain)

^b UNIVERSITY OF ZURICH   (Switzerland)

Author keywords

Alkylation; Amino acidesters; Lactams

Indexed keywords

ALPHA AMINO ACID; BETA LACTAM ANTIBIOTIC; ESTER;

ALKYLATION; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONFERENCE PAPER; CYCLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 0034725854     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(00)00406-3     Document Type: Conference Paper

References (59)

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28. (a) Palomo, C.; Aizpurua, J. M.; Legido, M.; Galarza, R.; Deya, P. M.; Dunogues, J.; Picard, J. P.; Ricci, A.; Seconi, G. Angew. Chem., Int. Ed. Engl. 1996, 35, 1239.
29. (b) Palomo, C.; Aizpurua, J. M.; Legido, M.; Mielgo, A.; Galarza, R. Chem. Eur. J. 1997, 3, 1432.
30. This observation is general for virtually all kinds of β-lactam compounds. For some examples and leading references, see: (a) Kametani, T. Heterocycles 1982, 17, 463. (b) Bose, A. K.; Manhas, M. S.; Mathur, A.; Wagle, D. R. In Recent Progress in the Chemical Synthesis of Antibiotics and Related Microbial Products; Lukacs, G., Ed.; Springer: New York, 1993; Vol. 2, p 551.
31. This observation is general for virtually all kinds of β-lactam compounds. For some examples and leading references, see: (a) Kametani, T. Heterocycles 1982, 17, 463. (b) Bose, A. K.; Manhas, M. S.; Mathur, A.; Wagle, D. R. In Recent Progress in the Chemical Synthesis of Antibiotics and Related Microbial Products; Lukacs, G., Ed.; Springer: New York, 1993; Vol. 2, p 551.
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34. Colson P.-J., Hegedus L.S. J. Org. Chem. 58:1993;5918.
35. The imine 12 can easily be prepared by simple mixing of 33% formaldehyde aqueous solution and the readily available C,C-bis(trimethylsilyl)methylamine. The latter can be prepared in gram quantities from commercially available N,N-dimethylcyanamide or cyanotrimethylsilane, see: (a) Picard, J. P.; Grelier, S.; Constantieux, T.; Dunoguès, J.; Aizpurua, J. M.; Palomo, C.; Petraud, M.; Barbe, B.; Lunnazi, L.; Leger, J. M. Organometallics 1993, 12, 1378, (b) Grelier, S.; Constantieux, T.; Deffieux, D.; Bordeau, M.; Dunogues, J.; Picard, J. P.; Palomo, C.; Aizpurua, J. M. Organometallics 1994, 13, 3711 and also from bis(trimethylsilyl)chloromethane, see: (c) Palomo, C.; Aizpurua, J. M.; Garcia, J. M.; Legido, M. J. Chem. Soc; Chem. Commun. 1991, 524.
36. The imine 12 can easily be prepared by simple mixing of 33% formaldehyde aqueous solution and the readily available C,C-bis(trimethylsilyl)methylamine. The latter can be prepared in gram quantities from commercially available N,N-dimethylcyanamide or cyanotrimethylsilane, see: (a) Picard, J. P.; Grelier, S.; Constantieux, T.; Dunoguès, J.; Aizpurua, J. M.; Palomo, C.; Petraud, M.; Barbe, B.; Lunnazi, L.; Leger, J. M. Organometallics 1993, 12, 1378, (b) Grelier, S.; Constantieux, T.; Deffieux, D.; Bordeau, M.; Dunogues, J.; Picard, J. P.; Palomo, C.; Aizpurua, J. M. Organometallics 1994, 13, 3711 and also from bis(trimethylsilyl)chloromethane, see: (c) Palomo, C.; Aizpurua, J. M.; Garcia, J. M.; Legido, M. J. Chem. Soc; Chem. Commun. 1991, 524.
37. The imine 12 can easily be prepared by simple mixing of 33% formaldehyde aqueous solution and the readily available C,C-bis(trimethylsilyl)methylamine. The latter can be prepared in gram quantities from commercially available N,N-dimethylcyanamide or cyanotrimethylsilane, see: (a) Picard, J. P.; Grelier, S.; Constantieux, T.; Dunoguès, J.; Aizpurua, J. M.; Palomo, C.; Petraud, M.; Barbe, B.; Lunnazi, L.; Leger, J. M. Organometallics 1993, 12, 1378, (b) Grelier, S.; Constantieux, T.; Deffieux, D.; Bordeau, M.; Dunogues, J.; Picard, J. P.; Palomo, C.; Aizpurua, J. M. Organometallics 1994, 13, 3711 and also from bis(trimethylsilyl)chloromethane, see: (c) Palomo, C.; Aizpurua, J. M.; Garcia, J. M.; Legido, M. J. Chem. Soc; Chem. Commun. 1991, 524.
38. (a) Evans, D. A.; Sjögren, E. B. Tetrahedron Lett. 1985, 26, 3783.
39. (b) Evans, D.A.; Sjögren, E. B. Tetrahedron Lett. 1985, 26, 3787.
40. For more detailed information on this subject, see: (a) Caperucci, A.; Ricci, A.; Seconi, G.; Dunogues, J.; Grelier, S.; Picard, J. P.; Palomo, C.; Aizpurua, J. M. J. Organomet. Chem. 1993, 458, C1. (b) Palomo, C.; Aizpurua, J. M.; Galarza, R. Chem. Commun. 1997, 233. For the low temperature generation of formaldimines, see: (c) Barluenga, A. M.; Bayon, A. M.; Asensio, G. J. Chem. Soc, Chem. Commun. 1983, 1109. (d) Barluenga, A. M.; Bayon, A. M.; Asensio, G. J. Chem. Soc, Chem. Commun. 1984, 427.
41. For more detailed information on this subject, see: (a) Caperucci, A.; Ricci, A.; Seconi, G.; Dunogues, J.; Grelier, S.; Picard, J. P.; Palomo, C.; Aizpurua, J. M. J. Organomet. Chem. 1993, 458, C1. (b) Palomo, C.; Aizpurua, J. M.; Galarza, R. Chem. Commun. 1997, 233. For the low temperature generation of formaldimines, see: (c) Barluenga, A. M.; Bayon, A. M.; Asensio, G. J. Chem. Soc, Chem. Commun. 1983, 1109. (d) Barluenga, A. M.; Bayon, A. M.; Asensio, G. J. Chem. Soc, Chem. Commun. 1984, 427.
42. For more detailed information on this subject, see: (a) Caperucci, A.; Ricci, A.; Seconi, G.; Dunogues, J.; Grelier, S.; Picard, J. P.; Palomo, C.; Aizpurua, J. M. J. Organomet. Chem. 1993, 458, C1. (b) Palomo, C.; Aizpurua, J. M.; Galarza, R. Chem. Commun. 1997, 233. For the low temperature generation of formaldimines, see: (c) Barluenga, A. M.; Bayon, A. M.; Asensio, G. J. Chem. Soc, Chem. Commun. 1983, 1109. (d) Barluenga, A. M.; Bayon, A. M.; Asensio, G. J. Chem. Soc, Chem. Commun. 1984, 427.
43. For more detailed information on this subject, see: (a) Caperucci, A.; Ricci, A.; Seconi, G.; Dunogues, J.; Grelier, S.; Picard, J. P.; Palomo, C.; Aizpurua, J. M. J. Organomet. Chem. 1993, 458, C1. (b) Palomo, C.; Aizpurua, J. M.; Galarza, R. Chem. Commun. 1997, 233. For the low temperature generation of formaldimines, see: (c) Barluenga, A. M.; Bayon, A. M.; Asensio, G. J. Chem. Soc, Chem. Commun. 1983, 1109. (d) Barluenga, A. M.; Bayon, A. M.; Asensio, G. J. Chem. Soc, Chem. Commun. 1984, 427.
44. -3 and an absolute structure parameter of 0.02(12). The enantiomorph was chosen using the known S-configuration of the benzylic stereocenter in the oxazolidine ring and was confirmed independently by the crystal-structure analysis. The crystallographic data (excluding structure factors) for structure 17f have been deposited at the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-113859 and can be obtained free of charge on application to the CCDC, 12 Union Road, Cambridge, CB2 1EZ, UK. [e-mail: deposit@ccdc.cam.ac.uk].
45. The acid chloride 15 was prepared according to the following sequence of reactions. The starting methyl ester was prepared according to Evans and Sjögren, see Ref. 15
46. Palomo C., Aizpurua J.M., Garcia J.M., Galarza R., Legido M., Urchegui R., Roman P., Luque A., Server-Carrio J., Linden A. J. Org. Chem. 62:1997;2070.
47. For N-deformylation procedures, see: (a) Farina, V.; Hauck, S. I.; Walker, D. Synlett 1992, 761. (b) Georg, G. I.; He, P.; Kant, J.; Wu, Z. J. Org. Chem. 1993, 58, 5771.
48. For N-deformylation procedures, see: (a) Farina, V.; Hauck, S. I.; Walker, D. Synlett 1992, 761. (b) Georg, G. I.; He, P.; Kant, J.; Wu, Z. J. Org. Chem. 1993, 58, 5771.
49. (a) Palomo, C.; Aizpurua, J. M.; Ganboa, I. In Enantioselective Synthesis of β-Amino Acids; Juaristi, E., Ed.; Wiley-VCH: New York, 1997; p 279.
50. (b) Palomo, C.; Aizpurua, J. M.; Ganboa, I.; Oiarbide, M. Amino Acids 1999, 16, 321.
51. For some examples on α-branched β-aminoalanine derivatives, see: (a) Hartwig, W.; Mittendorf, J. Synthesis 1991, 939. (b) Seebach, D.; Studer, A.; Pfammatter, E.; Widmer, H. Helv. Chim. Acta 1994, 77, 2035. (c) Jones, R. C. F.; Crockett, A. K.; Rees, D. C.; Gilbert, I. H. Tetrahedron Asymmetry 1994, 5, 1661. (d) Gilbert, I. H.; Rees, D. C.; Crockett, A. K.; Jones, R. C. F. Tetrahedron 1995, 51, 6315. (e) Badorrey, R.; Cativiela, C.; Diaz-de-Villegas, M. D.; Galvez, J. A. Tetrahedron Asymmetry 1995, 6, 2787. (f) Obrecht, D.; Karajiannis, H.; Lehmann, C.; Schönholzer, P.; Spiegler, C.; Müller, K. Helv. Chim. Acta 1995, 78, 703. (g) Acton, J. J., III; Jones, A. B. Tetrahedron Lett. 1996, 37, 4319.
52. For some examples on α-branched β-aminoalanine derivatives, see: (a) Hartwig, W.; Mittendorf, J. Synthesis 1991, 939. (b) Seebach, D.; Studer, A.; Pfammatter, E.; Widmer, H. Helv. Chim. Acta 1994, 77, 2035. (c) Jones, R. C. F.; Crockett, A. K.; Rees, D. C.; Gilbert, I. H. Tetrahedron Asymmetry 1994, 5, 1661. (d) Gilbert, I. H.; Rees, D. C.; Crockett, A. K.; Jones, R. C. F. Tetrahedron 1995, 51, 6315. (e) Badorrey, R.; Cativiela, C.; Diaz-de-Villegas, M. D.; Galvez, J. A. Tetrahedron Asymmetry 1995, 6, 2787. (f) Obrecht, D.; Karajiannis, H.; Lehmann, C.; Schönholzer, P.; Spiegler, C.; Müller, K. Helv. Chim. Acta 1995, 78, 703. (g) Acton, J. J., III; Jones, A. B. Tetrahedron Lett. 1996, 37, 4319.
53. For some examples on α-branched β-aminoalanine derivatives, see: (a) Hartwig, W.; Mittendorf, J. Synthesis 1991, 939. (b) Seebach, D.; Studer, A.; Pfammatter, E.; Widmer, H. Helv. Chim. Acta 1994, 77, 2035. (c) Jones, R. C. F.; Crockett, A. K.; Rees, D. C.; Gilbert, I. H. Tetrahedron Asymmetry 1994, 5, 1661. (d) Gilbert, I. H.; Rees, D. C.; Crockett, A. K.; Jones, R. C. F. Tetrahedron 1995, 51, 6315. (e) Badorrey, R.; Cativiela, C.; Diaz-de-Villegas, M. D.; Galvez, J. A. Tetrahedron Asymmetry 1995, 6, 2787. (f) Obrecht, D.; Karajiannis, H.; Lehmann, C.; Schönholzer, P.; Spiegler, C.; Müller, K. Helv. Chim. Acta 1995, 78, 703. (g) Acton, J. J., III; Jones, A. B. Tetrahedron Lett. 1996, 37, 4319.
54. For some examples on α-branched β-aminoalanine derivatives, see: (a) Hartwig, W.; Mittendorf, J. Synthesis 1991, 939. (b) Seebach, D.; Studer, A.; Pfammatter, E.; Widmer, H. Helv. Chim. Acta 1994, 77, 2035. (c) Jones, R. C. F.; Crockett, A. K.; Rees, D. C.; Gilbert, I. H. Tetrahedron Asymmetry 1994, 5, 1661. (d) Gilbert, I. H.; Rees, D. C.; Crockett, A. K.; Jones, R. C. F. Tetrahedron 1995, 51, 6315. (e) Badorrey, R.; Cativiela, C.; Diaz-de-Villegas, M. D.; Galvez, J. A. Tetrahedron Asymmetry 1995, 6, 2787. (f) Obrecht, D.; Karajiannis, H.; Lehmann, C.; Schönholzer, P.; Spiegler, C.; Müller, K. Helv. Chim. Acta 1995, 78, 703. (g) Acton, J. J., III; Jones, A. B. Tetrahedron Lett. 1996, 37, 4319.
55. For some examples on α-branched β-aminoalanine derivatives, see: (a) Hartwig, W.; Mittendorf, J. Synthesis 1991, 939. (b) Seebach, D.; Studer, A.; Pfammatter, E.; Widmer, H. Helv. Chim. Acta 1994, 77, 2035. (c) Jones, R. C. F.; Crockett, A. K.; Rees, D. C.; Gilbert, I. H. Tetrahedron Asymmetry 1994, 5, 1661. (d) Gilbert, I. H.; Rees, D. C.; Crockett, A. K.; Jones, R. C. F. Tetrahedron 1995, 51, 6315. (e) Badorrey, R.; Cativiela, C.; Diaz-de-Villegas, M. D.; Galvez, J. A. Tetrahedron Asymmetry 1995, 6, 2787. (f) Obrecht, D.; Karajiannis, H.; Lehmann, C.; Schönholzer, P.; Spiegler, C.; Müller, K. Helv. Chim. Acta 1995, 78, 703. (g) Acton, J. J., III; Jones, A. B. Tetrahedron Lett. 1996, 37, 4319.
56. For some examples on α-branched β-aminoalanine derivatives, see: (a) Hartwig, W.; Mittendorf, J. Synthesis 1991, 939. (b) Seebach, D.; Studer, A.; Pfammatter, E.; Widmer, H. Helv. Chim. Acta 1994, 77, 2035. (c) Jones, R. C. F.; Crockett, A. K.; Rees, D. C.; Gilbert, I. H. Tetrahedron Asymmetry 1994, 5, 1661. (d) Gilbert, I. H.; Rees, D. C.; Crockett, A. K.; Jones, R. C. F. Tetrahedron 1995, 51, 6315. (e) Badorrey, R.; Cativiela, C.; Diaz-de-Villegas, M. D.; Galvez, J. A. Tetrahedron Asymmetry 1995, 6, 2787. (f) Obrecht, D.; Karajiannis, H.; Lehmann, C.; Schönholzer, P.; Spiegler, C.; Müller, K. Helv. Chim. Acta 1995, 78, 703. (g) Acton, J. J., III; Jones, A. B. Tetrahedron Lett. 1996, 37, 4319.
57. For some examples on α-branched β-aminoalanine derivatives, see: (a) Hartwig, W.; Mittendorf, J. Synthesis 1991, 939. (b) Seebach, D.; Studer, A.; Pfammatter, E.; Widmer, H. Helv. Chim. Acta 1994, 77, 2035. (c) Jones, R. C. F.; Crockett, A. K.; Rees, D. C.; Gilbert, I. H. Tetrahedron Asymmetry 1994, 5, 1661. (d) Gilbert, I. H.; Rees, D. C.; Crockett, A. K.; Jones, R. C. F. Tetrahedron 1995, 51, 6315. (e) Badorrey, R.; Cativiela, C.; Diaz-de-Villegas, M. D.; Galvez, J. A. Tetrahedron Asymmetry 1995, 6, 2787. (f) Obrecht, D.; Karajiannis, H.; Lehmann, C.; Schönholzer, P.; Spiegler, C.; Müller, K. Helv. Chim. Acta 1995, 78, 703. (g) Acton, J. J., III; Jones, A. B. Tetrahedron Lett. 1996, 37, 4319.
58. (a) Palomo, C.; Aizpurua, J. M.; Cuevas, C.; Mielgo, A.; Galarza, R. Tetrahedron Lett. 1995, 36, 9027.
59. (b) Palomo, C.; Aizpurua, J. M.; Galarza, R.; Mielgo, A. Chem. Commun. 1996, 633.