A straightforward preparation of chiral 5-(aminomethyl)oxazole derivatives from α-amino esters and α-lithiated isocyanides

Chemical and Pharmaceutical Bulletin

Volumn 46, Issue 5, 1998, Pages 860-862

  Ohba, Masashi ^a   Kubo, Hiroyuki ^a   Seto, Shigeki ^a   Fujii, Tozo ^a   Ishibashi, Hiroyuki ^a  

^a KANAZAWA UNIVERSITY   (Japan)

Author keywords

(Aminomethyl)oxazole; Chiral synthesis; Enantiomeric purity; Isocyanide metalated; Amino ester

Indexed keywords

5 (AMINOMETHYL)OXAZOLE DERIVATIVE; CYANIDE; ESTER DERIVATIVE; LITHIUM DERIVATIVE; NATURAL PRODUCT; OXAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ENANTIOMER; RACEMIC MIXTURE; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0031835026     PISSN: 00092363     EISSN: None     Source Type: Journal    
DOI: 10.1248/cpb.46.860     Document Type: Article

References (34)

1. For reviews on α-metalated isocyanides, see a) Hoppe D., Angew. Chem., Int. Ed, Engl., 13, 789-804 (1974);
2. b) Schöllkopf U., ibid., 16, 339-348 (1977);
3. c) Idem, Pure Appl. Chem., 51, 1347-1355 (1979).
4. Schöllkopf U., Gerhart F., Angew. Chem., Int. Ed. Engl., 7, 805-806 (1968).
5. a) Schöllkopf U., Schöder R., Angew. Client., 83, 358-359 (1971);
6. b) Schröder R., Schöllkopf U., Blume E., Hoppe I., Justus Liebigs Ann. Chem., 1975, 533-546;
7. c) Henneke K.-W., Schöllkopf U., Neudecker T., ibid., 1979, 1370-1387;
8. d) Suzuki M., Iwasaki T., Miyoshi M., Okumura K., Matsumoto K., J. Org. Chem., 38, 3571-3575 (1973);
9. e) Matsumoto K., Suzuki M., Miyoshi M., Okumura K., Synthesis, 1974, 500-501.
10. For a review on oxazole alkaloids, see Jacobs H. M., Burke B. A., "The Alkaloids," Vol. 35, ed. by Brossi A., Academic Press, Inc., San Diego, 1989, Chapter 6.
11. For reviews on the chemistry of oxazoles, see a) Hassner A., Fischer B., Heteroeycles, 35, 1441-1465 (1993), and references cited therein;
12. b) Turchi I. J., Ind. Eng. Chem. Prod. Res. Dev., 20, 32-76 (1981);
13. Iddon B., Heterocycles, 37, 1321-1346 (1994).
14. Ohba M., Kubo H., Fujii T., Ishibashi H., Sargent M. V., Arbain D., Tetrahedron Lett., 38, 6697-6700 (1997).
15. Similar reactions leading to the formation of olefins have been reported: a) Meffre P., Gauzy L., Branquet E., Durand P., Le Goffic F., Tetrahedron, 52, 11215-11238 (1996);
16. b) Reginato G., Mordini A., Caracciolo M., J. Org. Chem., 62, 6187-6192 (1997).
17. For the synthesis of 5-(aminomethyl)-4-methoxycarbonyloxazoles from optically active N-Boc-α-amino acids and methyl isocyanoacetate by using diphenyl phosphorazidate, see a) Hamada Y., Shioiri T., Tetrahedron Lett., 23, 235-236 (1982);
18. b) Shioiri T., Hamada Y., Heterocycles, 27, 1035-1050 (1988).
19. Matsumoto K., Suzuki M., Miyoshi M., J. Org. Chem., 38, 2094-2096 (1973).
20. Still W. C., Kahn M., Mitra A., J. Org. Chem., 43, 2923-2925 (1978).
21. a) Casanova J., Jr., Schuster R. E., Werner N. D., J. Chem. Soc., 1963, 4280-4281;
22. b) Schuster R. E., Scott J. E., Casanova J., Jr., "Organic Syntheses," Coll. Vol. 5. ed. by Baumgarten H. E., John Wiley and Sons, Inc., New York, 1973, pp. 772-774.
23. Jackson H. L., McKusick B. C., "Organic Syntheses," Coll. Vol. 4, ed. by Rabjohn N., John Wiley and Sons. Inc., New York, 1963, pp. 438-440.
24. Tarbell D. S., Yamamoto Y., Pope B. M., Proc. Natl. Acad. Sci. U.S.A., 69, 730-732 (1972).
25. Schwyzer R., Sieber P., Kappeler H., Helv. Chim. Acta. 42, 2622-2624 (1959).
26. Boger J., Payne L. S., Perlow D. S., Lohr N. S., Poe M., Blaine E. H., Ulm E. H., Schorn T. W., LaMont B. I., Un T.-Y., Kawai M., Rich D. H., Veber D. F., J. Med. Chem., 28, 1779-1790 (1985).
27. a) Dhaon M. K., Olsen R. K., Ramasamy K., J. Org. Chem., 47, 1962-1965 (1982);
28. b) Luly J. R., Dellaria J. F., Plattner J. J., Soderquist J. L., Yi N., ibid., 52, 1487-1492 (1987).
29. Torrini I., Zecchini G. P., Agrosi F., Paradisi M. P., J. Heterocycl. Chem., 23, 1459-1463 (1986).
30. a) Garner P., Park J. M., J. Org. Chem., 52, 2361-2364 (1987);
31. b) Garner P., Park J. M., "Organic Syntheses," Vol. 70. ed. by Meyers A. I., John Wiley and Sons, Inc., New York, 1992, pp. 18-28;
32. c) McKillop A., Taylor R. J. K., Watson R. J., Lewis N., Synthesis, 1994, 31-33.
33. Miles N. J., Sammes P. G., Kennewell P. D., Westwood R., J. Chem. Soc., Perkin Trans. 1, 1985, 2299-2305.
34. Moriwake T., Hamano S., Saito S., Torii S., Chem. Lett., 1987, 2085-2088.