Cyclopropyl building blocks in organic synthesis, 51. An easy access to 1-azaspiropentane-2-carboxamides - The first derivatives of a new type of amino acids

European Journal of Organic Chemistry

Volumn , Issue 9, 1999, Pages 2017-2024

  Tamm, Markus ^b   Thutewohl, Michael ^b   Ricker, Carsten B ^b   Bes, M Teresa ^a,b   De Meijere, Armin ^b  

^a UNIVERSITY OF ZARAGOZA   (Spain)

^b UNIVERSITY OF GÖTTINGEN   (Germany)

Author keywords

Amino acids; Azaspiropentanes; Heterocycles; Peptides; Strained molecules

Indexed keywords

AMIDE; AMINO ACID DERIVATIVE; HETEROCYCLIC COMPOUND;

ANTIMICROBIAL ACTIVITY; ARTICLE; CONFORMATIONAL TRANSITION; DERIVATIZATION; DRUG SYNTHESIS; ENZYME INHIBITION; STRUCTURE ANALYSIS; X RAY CRYSTALLOGRAPHY;

EID: 0032827067     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1099-0690(199909)1999:9<2017::aid-ejoc2017>3.0.co;2-0     Document Type: Article

References (48)

1. Reviews: [1a] A. Alami, M. Calmes, J. Daunis, R. Jacquier, Bull. Soc. Chim. Fr. 1993, 130, 5-24.
2. [1b] C. H. Stammer, Tetrahedron 1990, 46, 2231-2254.
3. [1c] A. M. Serebryanyi, G. A. Krasheninnikova, L. V. Vakhina, Biochemistry (Moscow) 1995, 60, 759-766, and references cited therein.
4. [2a] N. Andres, H. Wolf, H. Zähner, E. Rössner, A. Zeeck, W. A. König, V. Sinnwell, Helv. Chim. Acta 1989, 72, 426-437.
5. [2b] E. Rössner, A. Zeeck, W. A. König, Angew. Chem. 1990, 102, 84-85; Angew. Chem. Int. Ed. Engl. 1990, 29, 64-65.
6. [2b] E. Rössner, A. Zeeck, W. A. König, Angew. Chem. 1990, 102, 84-85; Angew. Chem. Int. Ed. Engl. 1990, 29, 64-65.
7. [2c] J. Zindel, A. de Meijere, J. Org. Chem. 1995, 60, 2968-2973.
8. [3a] M. C. Pirrung, J. Cao, J. Chen, J. Org. Chem. 1995, 60, 5790-5794.
9. [3b] M. C. Pirrung, H. Han, J. Chen, J. Org. Chem. 1996, 61, 4527-4531.
10. [3c] M. C. Pirrung, L. M. Kaiser, J. Chen, Biochemistry 1993, 32, 7445-7450.
11. K. Burgess, K.-K. Ho, D. Moye-Sherman, Synlett 1994, 575-583.
12. J. Salaün, M. S. Baird, Curr. Med. Chem. 1995, 2, 511-542.
13. [6a] Z. Huang, Y.-B. He, K. Raynor, M. Tallent, T. Reisine, M. Goodman, J. Am. Chem. Soc. 1992, 114, 9390-9401.
14. [6b] Y.-F. Zhu, T. Yamazaki, J. W. Tsang, S. Lok, M. Goodman, J. Org. Chem. 1992, 57, 1074-1081.
15. M. Shimura, M. Iwata, S. Omoto, Y. Sekizawa, Agric. Biol. Chem. 1979, 43, 2279-2281.
16. [8a] D. H. Aue, R. B. Lorens, G. S. Helwig, Tetrahedron Lett. 1973, 48, 4795-4798.
17. [8b] D. H. Aue, R. B. Lorens, G. S. Helwig. J. Org. Chem. 1979, 44, 1202-1207.
18. [8c] J. K. Crandall, W. W. Conover, J. Chem. Soc., Chem. Commun. 1973, 33-34.
19. [8d] J. K. Crandall, W. W. Conover, J. Org. Chem. 1974, 39, 63-66.
20. [8e] O. Tsuge, T. Ohnishi, H. Watanabe, Heterocycles 1981, 16, 2085-2090.
21. [8f] O. Tsuge, H. Watanabe, Heterocycles 1976, 4, 1905-1908.
22. [8g] O. Tsuge, H. Watanabe, Heterocycles 1977, 7, 907-912.
23. [8h] O. Tsuge, H. Watanabe, Y. Kiryu, Bull. Chem. Soc. Jpn. 1979, 52, 3387-3390.
24. [8i] T. Tlili, J. Soc. Chim. Tunis. 1988, 2, 3-7.
25. In general, aziridines possess alkylating properties. Because of this character, many natural and unnatural aziridine-containing compounds show biological activities. See: A. R. Katritzky, C. W. Rees, E. F. Criven, Comprehensive Heterocyclic Chemistry II, Pergamon Press, New York, 1996, vol. 1A, pp. 58-60 and references cited therein.
26. [10a] P. Dauban, L. Dubois, M. E. T. H. Dau, R. H. Dodd, J. Org. Chem. 1995, 60, 2035-2043.
27. [10b] D. Tanner, Angew. Chem. 1994, 106, 625-646; Angew. Chem. Int. Ed. Engl. 1994, 33, 599-620, and references cited therein.
28. [10b] D. Tanner, Angew. Chem. 1994, 106, 625-646; Angew. Chem. Int. Ed. Engl. 1994, 33, 599-620, and references cited therein.
29. [10c] M. Goodman, Chem. Biol. 1994, 231.
30. T. Liese, F. Seyed-Mahdavi, A. de Meijere, Org. Synth. 1990, 69, 148-153.
31. [12a] M. Es-Sayed, C. Gratkowski, N. Krass, A. I. Meyers, A. de Meijere, Synlett 1992, 3, 962-964.
32. [12b] M. Es-Sayed, C. Gratkowski, N. Krass, A. I. Meyers, A. de Meijere, Tetrahedron Lett. 1993, 34, 289-292.
33. [12c] L. Wessjohann, N. Krass, D. Yu, A. de Meijere, Chem. Ber. 1992, 125, 867-882.
34. [12d] Reviews see: A. de Meijere, L. Wessjohann, Synlett 1990, 1, 20-32; A. de Meijere in New Aspects of Organic Chemistry II, Proceedings of the Fifth International Kyoto Conference on New Aspects of Organic Chemistry - IKCOC 5, Kyoto Nov. 11-Nov. 15 1991 (Ed.: Y. Ohshiro) Kodansha, Tokyo, 1992, pp. 181-213; A. de Meijere, L. Hadjiarapoglou, S. I. Kozhushkov, Top. Curr. Chem., in press.
35. [12d] Reviews see: A. de Meijere, L. Wessjohann, Synlett 1990, 1, 20-32; A. de Meijere in New Aspects of Organic Chemistry II, Proceedings of the Fifth International Kyoto Conference on New Aspects of Organic Chemistry - IKCOC 5, Kyoto Nov. 11-Nov. 15 1991 (Ed.: Y. Ohshiro) Kodansha, Tokyo, 1992, pp. 181-213; A. de Meijere, L. Hadjiarapoglou, S. I. Kozhushkov, Top. Curr. Chem., in press.
36. [12d] Reviews see: A. de Meijere, L. Wessjohann, Synlett 1990, 1, 20-32; A. de Meijere in New Aspects of Organic Chemistry II, Proceedings of the Fifth International Kyoto Conference on New Aspects of Organic Chemistry - IKCOC 5, Kyoto Nov. 11-Nov. 15 1991 (Ed.: Y. Ohshiro) Kodansha, Tokyo, 1992, pp. 181-213; A. de Meijere, L. Hadjiarapoglou, S. I. Kozhushkov, Top. Curr. Chem., in press.
37. This rearrangement is analogous to the one previously observed for the benzophenonimine adducts of methyl 2-chloro-2-cyclopropylideneacetate and its substituted analogs: L. Wessjohann, K. Giller, B. Zuck, L. Skattebøl, A. de Meijere, J. Org. Chem. 1993, 58, 6442-6450.
38. The reaction of 2-bromo-2-(4′-tert-butylcyclohexyridene)acetates with benzylamine under high pressure has recently been reported to give spirocyclohexane-annelated aziridinecarboxylates in very good yields: A. Yu. Rulev, J. Maddalumo, G. Plé, J.-C. Plaquevent, L. Duhamel, J. Chem. Soc., Perkin Trans. 1 1998, 1397-1401; see also: A. Yu. Rulev, Uspekhi Khim. 1998, 67, 317-332; Russ. Chem. Rev. 1998, 67, 279-293.
39. The reaction of 2-bromo-2-(4′-tert-butylcyclohexyridene)acetates with benzylamine under high pressure has recently been reported to give spirocyclohexane-annelated aziridinecarboxylates in very good yields: A. Yu. Rulev, J. Maddalumo, G. Plé, J.-C. Plaquevent, L. Duhamel, J. Chem. Soc., Perkin Trans. 1 1998, 1397-1401; see also: A. Yu. Rulev, Uspekhi Khim. 1998, 67, 317-332; Russ. Chem. Rev. 1998, 67, 279-293.
40. The reaction of 2-bromo-2-(4′-tert-butylcyclohexyridene)acetates with benzylamine under high pressure has recently been reported to give spirocyclohexane-annelated aziridinecarboxylates in very good yields: A. Yu. Rulev, J. Maddalumo, G. Plé, J.-C. Plaquevent, L. Duhamel, J. Chem. Soc., Perkin Trans. 1 1998, 1397-1401; see also: A. Yu. Rulev, Uspekhi Khim. 1998, 67, 317-332; Russ. Chem. Rev. 1998, 67, 279-293.
41. Unsubstituted aziridinecarboxamide has been found to be a reasonably stable compound, cf.: K. Jähnisch, E. Schmitz, E. Gründemann, J. Prakt. Chem. 1979, 321, 712-720.
42. 2 = 1.031. 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-100381. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (Fax: int. code + 44-1223/336-033; E-mail: deposit@ccdc.cam.ac.uk).
43. 2 = 1.031. 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-100381. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (Fax: int. code + 44-1223/336-033; E-mail: deposit@ccdc.cam.ac.uk).
44. R. Boese, D. Bläser, K. Gomann, U. H. Brinker, J. Am. Chem. Soc. 1989, 111, 1501-1503.
45. R. Boese, T. Miebach, A. de Meijere, J. Am. Chem. Soc. 1991, 113, 1743-1748.
46. M. Tamm, M. Nötzel, A. de Meijere, J. Org. Chem., submitted.
47. [11] is commercially available from Merck KGaA, Frankfurter Str. 250, D-64293 Darmstadt, Germany.
48. L. Wessjohann, N. Krass, D. Yu, A. de Meijere, Chem. Ber. 1992, 125, 867-882.