A new and efficient access to oxazoline-5-carboxylates and amino acid derivatives with cyclopropyl groups

Journal of Organic Chemistry

Volumn 65, Issue 12, 2000, Pages 3850-3852

  Nötzel, Marcus W ^a   Tamm, Markus ^a   Labahn, Thomas ^a   Noltemeyer, Mathias ^a   Es Sayed, Mazen ^b   De Meijere, Armin ^a  

^a UNIVERSITY OF GÖTTINGEN   (Germany)

^b BAYER AG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID DERIVATIVE; CYCLOPROPANE DERIVATIVE; OXAZOLINE DERIVATIVE;

CARBON NUCLEAR MAGNETIC RESONANCE; CRYSTAL STRUCTURE; DRUG ISOLATION; DRUG SYNTHESIS; ENZYME INHIBITION; MOLECULAR INTERACTION; NOTE; X RAY CRYSTALLOGRAPHY;

AMINO ACIDS; CARBOXYLIC ACIDS; CYCLOPROPANES; INDICATORS AND REAGENTS; MOLECULAR CONFORMATION; OXAZOLES; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0034674435     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990170y     Document Type: Note

References (37)

1. Part 56 in the series "Cyclopropyl Building Blocks in Organic Synthesis". For Part 55 see: Winsel, H.; Gazizova, V.; Kulinkovich, O.; Pavlov, V.; de Meijere, A. Synlett 1999, 1999-2003. For Part 54 see: de Meijere, A.; Nüske, H.; Es-Sayed, M.; Schroen, M.; Labahn, T.; Bräse, S. Angew. Chem. 1999, 111, 3881-3884; Angew. Chem., Int. Ed. Engl. 1999, 38, 3669-3672.
2. Part 56 in the series "Cyclopropyl Building Blocks in Organic Synthesis". For Part 55 see: Winsel, H.; Gazizova, V.; Kulinkovich, O.; Pavlov, V.; de Meijere, A. Synlett 1999, 1999-2003. For Part 54 see: de Meijere, A.; Nüske, H.; Es-Sayed, M.; Schroen, M.; Labahn, T.; Bräse, S. Angew. Chem. 1999, 111, 3881-3884; Angew. Chem., Int. Ed. Engl. 1999, 38, 3669-3672.
3. Part 56 in the series "Cyclopropyl Building Blocks in Organic Synthesis". For Part 55 see: Winsel, H.; Gazizova, V.; Kulinkovich, O.; Pavlov, V.; de Meijere, A. Synlett 1999, 1999-2003. For Part 54 see: de Meijere, A.; Nüske, H.; Es-Sayed, M.; Schroen, M.; Labahn, T.; Bräse, S. Angew. Chem. 1999, 111, 3881-3884; Angew. Chem., Int. Ed. Engl. 1999, 38, 3669-3672.
4. Part 56 in the series "Cyclopropyl Building Blocks in Organic Synthesis". For Part 55 see: Winsel, H.; Gazizova, V.; Kulinkovich, O.; Pavlov, V.; de Meijere, A. Synlett 1999, 1999-2003. For Part 54 see: de Meijere, A.; Nüske, H.; Es-Sayed, M.; Schroen, M.; Labahn, T.; Bräse, S. Angew. Chem. 1999, 111, 3881-3884; Angew. Chem., Int. Ed. Engl. 1999, 38, 3669-3672.
5. (a) Pirrung, M. C.; Cao, J.; Chen, J. J. Org. Chem. 1995, 60, 5790-5794.
6. (b) Pirrung, M. C.; Han, H.; Chen, J. J. Org. Chem. 1996, 61, 4527-4531.
7. (c) Pirrung, M. C.; Kaiser, L. M., Chen, J. Biochemistry 1993, 32, 7445-7450.
8. Burgess, K.; Ho, K.-K.; Moye-Sherman, D. Synlett 1994, 575-583.
9. (a) Salaün, J. Top. Curr. Chem. 1999, 207, 1-88.
10. (b) Salaün, J.; Baird. M. S. Curr. Med. Chem. 1995, 2, 511-542.
11. (c) Huang, Z.; He, Y.-B.; Raynor, K.; Tallent, M.; Reisine, T.; Goodman, M. J. Am. Chem. Soc. 1992, 114, 9390-9401.
12. (d) Zhu, Y.-F.; Yamazaki, T.; Tsang, J. W.; Lok, S.; Goodman, M. J. Org. Chem. 1992, 57, 1074-1081.
13. For reviews see: (a) de Meijere, A.; Wessjohann, L. Synlett 1990, 20-32. (b) de Meijere, A. In New Aspects of Organic Chemistry II, Proceedings of the Fifth International Kyoto Conference on New Aspects of Organic Chemistry-IKCOC 5, Kyoto, Nov 11-15 1991; Oshiro, Y., Ed.; Kodansha: Tokyo, 1992; p 181. (c) de Meijere, A.; Kozhushkov, S. I.; Hadjiarapoglou, L. Top. Curr. Chem. 1999, 207, 149-227.
14. For reviews see: (a) de Meijere, A.; Wessjohann, L. Synlett 1990, 20-32. (b) de Meijere, A. In New Aspects of Organic Chemistry II, Proceedings of the Fifth International Kyoto Conference on New Aspects of Organic Chemistry-IKCOC 5, Kyoto, Nov 11-15 1991; Oshiro, Y., Ed.; Kodansha: Tokyo, 1992; p 181. (c) de Meijere, A.; Kozhushkov, S. I.; Hadjiarapoglou, L. Top. Curr. Chem. 1999, 207, 149-227.
15. For reviews see: (a) de Meijere, A.; Wessjohann, L. Synlett 1990, 20-32. (b) de Meijere, A. In New Aspects of Organic Chemistry II, Proceedings of the Fifth International Kyoto Conference on New Aspects of Organic Chemistry-IKCOC 5, Kyoto, Nov 11-15 1991; Oshiro, Y., Ed.; Kodansha: Tokyo, 1992; p 181. (c) de Meijere, A.; Kozhushkov, S. I.; Hadjiarapoglou, L. Top. Curr. Chem. 1999, 207, 149-227.
16. (a) Wessjohann, L.; Krass, N.; Yu, D.; de Meijere, A. Chem. Ber. 1992, 125, 867-882.
17. (b) Tamm, M.; Thutewohl, M.; Ricker, C.; Bes, M. T.; de Meijere, A. Eur. J. Org. Chem. 1999, 2017-2024.
18. (a) Es-Sayed, M.; Gratkowski, C.; Krass, N.; de Meijere, A. Synlett 1992, 962-964.
19. (b) Es-Sayed, M.; Gratkowski, C.; Krass, N.; Meyers, A. I.; de Meijere, A. Tetrahedron Lett. 1993, 34, 289-292.
20. Wessjohann, L.; Giller, K.; Zuck, B.; Skattebøl, L.; de Meijere, A. J. Org. Chem. 1993, 58, 6442-6450.
21. Liese, T.; Seyed-Mahdavi, F.; de Meijere, A. Org. Synth. 1990, 69, 148-153.
22. de Meijere, A.; Teichmann, S.; Yu, D.; Kopf, J.; Oly, M.; von Thienen, N. Tetrahedron 1989, 45, 2957-2972.
23. For examples see: (a) Gabriel, S.; Elfeldt, P. Chem. Ber. 1891, 24, 3213-3228. (b) Cassebaum, H.; Uhlig, K. J. Prakt. Chem. 1973, 315, 1057-1066. (c) Flouzat, C.; Guillaumet, G. Synthesis 1990, 64- 66. (d) Nishiyama, H.; Yamaguchi, S.; Kondo, M.; Itoh, K. J. Org. Chem. 1992, 57, 4306-4309. (e) Perry, J. R.; Wilson, B. D. J. Org. Chem. 1992, 57, 6351-6354. (f) Minami, T.; Isonaka, T.; Okada, Y.; Ichikawa, J. J. Org. Chem. 1993, 58, 7009-7015.
24. For examples see: (a) Gabriel, S.; Elfeldt, P. Chem. Ber. 1891, 24, 3213-3228. (b) Cassebaum, H.; Uhlig, K. J. Prakt. Chem. 1973, 315, 1057-1066. (c) Flouzat, C.; Guillaumet, G. Synthesis 1990, 64- 66. (d) Nishiyama, H.; Yamaguchi, S.; Kondo, M.; Itoh, K. J. Org. Chem. 1992, 57, 4306-4309. (e) Perry, J. R.; Wilson, B. D. J. Org. Chem. 1992, 57, 6351-6354. (f) Minami, T.; Isonaka, T.; Okada, Y.; Ichikawa, J. J. Org. Chem. 1993, 58, 7009-7015.
25. For examples see: (a) Gabriel, S.; Elfeldt, P. Chem. Ber. 1891, 24, 3213-3228. (b) Cassebaum, H.; Uhlig, K. J. Prakt. Chem. 1973, 315, 1057-1066. (c) Flouzat, C.; Guillaumet, G. Synthesis 1990, 64-66. (d) Nishiyama, H.; Yamaguchi, S.; Kondo, M.; Itoh, K. J. Org. Chem. 1992, 57, 4306-4309. (e) Perry, J. R.; Wilson, B. D. J. Org. Chem. 1992, 57, 6351-6354. (f) Minami, T.; Isonaka, T.; Okada, Y.; Ichikawa, J. J. Org. Chem. 1993, 58, 7009-7015.
26. For examples see: (a) Gabriel, S.; Elfeldt, P. Chem. Ber. 1891, 24, 3213-3228. (b) Cassebaum, H.; Uhlig, K. J. Prakt. Chem. 1973, 315, 1057-1066. (c) Flouzat, C.; Guillaumet, G. Synthesis 1990, 64- 66. (d) Nishiyama, H.; Yamaguchi, S.; Kondo, M.; Itoh, K. J. Org. Chem. 1992, 57, 4306-4309. (e) Perry, J. R.; Wilson, B. D. J. Org. Chem. 1992, 57, 6351-6354. (f) Minami, T.; Isonaka, T.; Okada, Y.; Ichikawa, J. J. Org. Chem. 1993, 58, 7009-7015.
27. For examples see: (a) Gabriel, S.; Elfeldt, P. Chem. Ber. 1891, 24, 3213-3228. (b) Cassebaum, H.; Uhlig, K. J. Prakt. Chem. 1973, 315, 1057-1066. (c) Flouzat, C.; Guillaumet, G. Synthesis 1990, 64- 66. (d) Nishiyama, H.; Yamaguchi, S.; Kondo, M.; Itoh, K. J. Org. Chem. 1992, 57, 4306-4309. (e) Perry, J. R.; Wilson, B. D. J. Org. Chem. 1992, 57, 6351-6354. (f) Minami, T.; Isonaka, T.; Okada, Y.; Ichikawa, J. J. Org. Chem. 1993, 58, 7009-7015.
28. For examples see: (a) Gabriel, S.; Elfeldt, P. Chem. Ber. 1891, 24, 3213-3228. (b) Cassebaum, H.; Uhlig, K. J. Prakt. Chem. 1973, 315, 1057-1066. (c) Flouzat, C.; Guillaumet, G. Synthesis 1990, 64- 66. (d) Nishiyama, H.; Yamaguchi, S.; Kondo, M.; Itoh, K. J. Org. Chem. 1992, 57, 4306-4309. (e) Perry, J. R.; Wilson, B. D. J. Org. Chem. 1992, 57, 6351-6354. (f) Minami, T.; Isonaka, T.; Okada, Y.; Ichikawa, J. J. Org. Chem. 1993, 58, 7009-7015.
29. Crystallographic data for the structures reported in this paper have been deposited with the Cambridge Crystallographic Centre as supplementary publication CCDC-113834 (5a) and CCDC-135542 (5s). Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge, CB2 1EZ, U.K. (a) Sheldrick, G. M. Acta Crystallogr., Sect. A 1990, 46, 467. (b) Sheldrick, G. M. SHELXL-93, program for crystal structure refinement: University of Göttingen: Göttingen, 1993.
30. Crystallographic data for the structures reported in this paper have been deposited with the Cambridge Crystallographic Centre as supplementary publication CCDC-113834 (5a) and CCDC-135542 (5s). Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge, CB2 1EZ, U.K. (a) Sheldrick, G. M. Acta Crystallogr., Sect. A 1990, 46, 467. (b) Sheldrick, G. M. SHELXL-93, program for crystal structure refinement: University of Göttingen: Göttingen, 1993.
31. (a) Holton, R. A.; Somoza, C.; Kim, H.-B.; Liang, F.; Biediger, R. J.; Boatman, P. D.; Shindo, M.; Smith, C. C.; Kim, S.; Nadizadeh, H.; Suzuki, Y.; Tao, C.; Vu, P.; Tang, S.; Zhang, P.; Murthi, K. K.; Gentile, L. N.; Liu, J. H. J. Am. Chem. Soc. 1994, 116, 1597-1599.
32. (b) Holton, R. A.; Somoza, C.; Kim, H.-B.; Liang, F.; Biediger, R. J.; Boatman, P. D.; Shindo, M.; Smith, C. C.; Kim, S.; Nadizadeh, H.; Suzuki, Y.; Tao, C.; Vu, P.; Tang, S.; Zhang, P.; Murthi, K. K.; Gentile, L. N.; Liu, J. H. J. Am. Chem. Soc. 1994, 116, 1599-1600.
33. (c) Georg, G. I.; Harriman, G. C. B.; Hepperle, M.; Himes, R. H. Bioorg. Med. Chem. Lett. 1994, 4, 1381-1384.
34. (d) Georg, G. I.; Harriman, G. C. B.; Hepperle, M.; Glowers, J. S.; Vander Velde, D. G.; Himes, R. H. J. Org. Chem. 1996, 61, 2664-2676.
35. (e) Li, L.; Thomas, S. A.; Klein, C. M.; Yeung, C. M.; Maring C. J.; Grampovnik, D. J.; Lartey, A.; Plattner, J. J. J. Med. Chem. 1994, 37, 2655-2663.
36. The immediate precursor to 1a, 1-chloro-1-(trichloroethenyl)-cyclopropane, is commercially available from Merck-Schuchardt.
37. Autorenkollektiv Organikum, 15. Aufl., VEB Dt.; Verlag der Wissenschaften: Berlin 1984.