The synthesis of novel cyclic β-amino acids as intermediates for the preparation of bicyclic β-lactams

European Journal of Organic Chemistry

Volumn , Issue 9, 1999, Pages 2433-2441

  Maison, Wolfgang ^a   Kosten, Marc ^a   Charpy, Audrey ^b   Kintscher Langenhagen, Jürgen ^a   Schlemminger, Imre ^a   Lützen, Arne ^a   Westerhoff, Ole ^a   Martens, Jürgen ^a  

^a UNIVERSITY OF OLDENBURG   (Germany)

^b UNIVERSITÉ DE REIMS CHAMPAGNE ARDENNE   (France)

Author keywords

Amino acids; Heterocycles; Lactams; Nitrogen heterocycles; Schiff bases

Indexed keywords

BETA AMINO ACID; BETA LACTAM DERIVATIVE; CARBACEPHEM DERIVATIVE; HETEROCYCLIC AMINE; ISOPENAM DERIVATIVE; ISOPENICILLIN G; PENAM DERIVATIVE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CHIRALITY; DIASTEREOISOMER; NUCLEAR OVERHAUSER EFFECT; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS;

EID: 0032848817     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1099-0690(199909)1999:9<2433::aid-ejoc2433>3.0.co;2-x     Document Type: Article

References (47)

1. [1a] O. W. Griffith, Ann. Rev. Biochem. 1986, 55, 855-878.
2. [1b] A. K. Thakur, R. Kishore, Tetrahedron Lett. 1998, 39, 9553-9556.
3. [1c] E. Benedetti, Biopolymers 1996, 40, 3-44.
4. [1d] D. Seebach, S. Abele, K. Gademann, G. Guichard, T. Hintermann, B. Jaun, J. L. Matthews, J. V. Schreiber, Helv. Chim. Acta 1998, 81, 932-982.
5. [2a] O. Muraoka, B. Z. Zheng, K. Okumura, E. Tabata, G. Tanabe, M. Kubo, J. Chem. Soc., Perkin Trans. 1, 1997, 113-119.
6. [2b] C. Herdeis, W. A. Held, A. Kirfel, F. Schwabenländer, Tetrahedron 1996, 52, 6409-6420.
7. [2c] C. Morley, D. W. Knight, A. C. Share, J. Chem. Soc., Perkin Trans. 1, 1994, 2903-2907.
8. [2d] K. S. Patrick, C. D. Kilts, G. R. Breese, J. Med. Chem. 1981, 24, 1237-1240.
9. [3a] T. L. Gilchrist, A. Rahman, J. Chem. Soc., Perkin Trans. 1, 1998, 1203-1207. R. Sammer, J. Blumbach, K. H. Scheunemann, Angew. Chem. 1985, 97, 183-205; Angew. Chem., Int. Ed. Engl. 1985, 24, 180-202.
10. [3a] T. L. Gilchrist, A. Rahman, J. Chem. Soc., Perkin Trans. 1, 1998, 1203-1207. R. Sammer, J. Blumbach, K. H. Scheunemann, Angew. Chem. 1985, 97, 183-205; Angew. Chem., Int. Ed. Engl. 1985, 24, 180-202.
11. [3a] T. L. Gilchrist, A. Rahman, J. Chem. Soc., Perkin Trans. 1, 1998, 1203-1207. R. Sammer, J. Blumbach, K. H. Scheunemann, Angew. Chem. 1985, 97, 183-205; Angew. Chem., Int. Ed. Engl. 1985, 24, 180-202.
12. [3b] D. R. Bender, L. F. Bjeldanes, D. R. Knapp, H. Rapoport, J. Org. Chem. 1975, 40, 1264-1269.
13. [4a] D. M. Brunwill, G. Lowe, J. Parker, J. Chem. Soc. (C), 1971 3756-3762.
14. [4b] J.-F Berrien, M.-A. Billion, H.-P. Husson, J. Royer, J. Org. Chem. 1995, 60, 2922-2924.
15. [5a] C. Gao, N. X. Chin, H. C. Neu, J. Antimicrob. Chemother. 1988, 22, 155-158. L. C. Blaszczak, R. F. Brown, G. K. Cook, W. J. Hornback, R. C. Hoying, J. M. Indelicato, C. L. Jordan, A. S. Katner, M. D. Kinnick, J. H. McDonald, C. E. Passini, J. Med. Chem. 1990, 33, 1656-1662.
16. [5a] C. Gao, N. X. Chin, H. C. Neu, J. Antimicrob. Chemother. 1988, 22, 155-158. L. C. Blaszczak, R. F. Brown, G. K. Cook, W. J. Hornback, R. C. Hoying, J. M. Indelicato, C. L. Jordan, A. S. Katner, M. D. Kinnick, J. H. McDonald, C. E. Passini, J. Med. Chem. 1990, 33, 1656-1662.
17. [5b] T. Ogasa, H. Saito, Y. Hashimoto, K. Sato, T. Hirata, Chem. Pharm. Bull. 1989, 37, 315-321.
18. [5c] S. Uyeo, H. Ona, Chem. Pharm. Bull. 1980, 28, 1563-1577.
19. [5d] R. A. Firestone, J. L. Fahey, N. S. Maciejewicz, G. S. Patel, B. G. Christensen, J. Med. Chem. 1977, 20, 551-556.
20. [6a] M. I. Page, A. P. Laws, Chem. Comm. 1998, 1609-1617.
21. [6b] F. Toda, H. Miyamoto, R. Matsukawa, J. Chem. Soc., Perkin Trans. 1, 1992, 1461-1462.
22. J. Martens, J. Kintscher, W. Arnold, Synthesis 1991, 497-498.
23. [8a] G. Krüger, Houben-Weyl, 4th ed., vol. E5, Georg Thieme Verlag, Stuttgart, 1985, p. 557.
24. [8b] G. Cardillo, C. Tomasini, Chem. Soc. Rev. 1996, 25, 117-128.
25. [8c] E. Juaristi, Enantioselective Synthesis of β-Amino Acids, Wiley-VCH, New York, 1997.
26. [8d] D. C. Cole, Tetrahedron 1994, 50, 9517-9582.
27. [9a] T. B. Johnson, J. E. Livak, J. Am. Chem. Soc. 1936, 58, 799-303.
28. [9b] H. Fukawa, Y. Terao, K. Achiwa, M. Sekiya, Chem. Lett. 1982, 231-232.
29. [9c] H. Fukawa, Y. Terao, K. Achiwa, M. Sekiya, Chem. Pharm. Bull. 1983, 31, 94-99.
30. [10a] W. M. Rodionov, E. A. Postovskaja, J. Am. Chem. Soc. 1929, 51, 841-846.
31. [10b] W. M. Rodionov, J. Am. Chem. Soc. 1929, 51, 847-852.
32. J. C. Pelletier, M. P. Cava, J. Org. Chem. 1987, 52, 616-622.
33. [12a] J. R. Smolanoff (Rohm & Haas Co.), U.S. Pat. 751, 932, 1976.
34. [12b] N. D. Kimpe, M. Keppens, G. Fonk, Chem. Comm. 1996, 635-636.
35. H. Zondler, W. Pfleiderer, Liebigs Ann. Chem. 1972, 759, 84-106.
36. W. Arnold, Ph. D. Dissertation, Univ. of Oldenburg, 1992.
37. D. Seebach, J. D. Aebi, M. Coquoz, R. Naef, Helv. Chim. Acta 1987, 70, 1194-1216.
38. [16a] J. V. Paukstelis, R. M. Hammaker, Tetrahedron Lett. 1969, 32, 3557-3560.
39. [16b] J. V. Paukstelis, L. L. Lambing, Tetrahedron Lett. 1970, 33, 299-302.
40. E. L. Eliel, S. H. Wilen, Stereochemistry of Organic Compounds, John Wiley & Sons, Inc., New York, 1994.
41. T. W. Greene, P. G. M. Wuts, Protective Groups in Organic Synthesis, 2nd ed.; Wiley-Interscience; New York, 1991; pp 349-350.
42. [19a] J. C. Sheehan, E. J. Corey, Org. React. 1957, 9, 388-408.
43. [19b] F. Moll, Arch. Pharm. Weinheim 1968, 301, 230-238.
44. H. Huang, N. Iwasawa, T. Mukaiyama, Chem. Lett. 1984, 1465-1466.
45. S. Kobayashi, T. Iimori, T. Izawa, M. Ohno, J. Am. Chem. Soc. 1981, 103, 2406-2408.
46. [22a] G. F. H. Green, J. E. Page, S. E. Staniforth, J. Chem. Soc. 1965 1595-1605.
47. [22b] P. H. Crackett, C. M. Pant, R. J. Stoodlev, J. Chem. Soc. 1984, 2785-2793.