Lewis acid catalyzed formal [3 + 2] cycloaddition of 5-alkoxyoxazoles and thiazoles

Reviews on Heteroatom Chemistry

Volumn 21, Issue , 2000, Pages 195-221

  Suga, Hiroyuki ^a   Ibata, Toshikazu ^b  

^a SHINSHU UNIVERSITY   (Japan)

^b OSAKA UNIVERSITY   (Japan)

Author keywords

Cycloaddition; Oxazole; Stereoselectivity; Thiazole

Indexed keywords

EID: 0033478875     PISSN: 09156151     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (39)

1. H. C. van der Plas: Ring Transformation of Heterocycles (Academic Press, London, 1973) Vol. 1, p. 314.
2. A. R. Katrizky: Advances in Heterocyclic Chemistry (Academic Press, New York, 1974) Vol. 17.
3. I. J. Turchi: The Chemistry of Heterocyclic Compounds (Ed.) I. J. Turchi (Wiley, New York, 1986) Vol. 45, pp. 127-134.
4. I. J. Turchi and M. J. S. Dewar: Chem. Rev. 75 389 (1975).
5. D. L. Boger and S. M. Weinreb: Hetero Diels-Alder Methodology in Organic Synthesis, as Vol. 47 in Organic Chemistry, A Series of Monographs (Ed.) H. H. Wasserman (Academic Press, New York, 1987) Chap. 10, pp. 300-310.
6. T. Ibata, Y. Isogami, S. Nakano and H. Tamura: J. Chem. Soc., Chem. Commun. 1692 (1986).
7. T. Ibata, Y. Isogami, H. Nakawa, H. Tamura, H. Suga, X. Shi and H. Fujieda: Bull. Chem. Soc. Jpn. 65 1771 (1992).
8. T. Ibata, Y. Isogami and H. Tamura: Chem. Lett. 1551 (1988).
9. T. Ibata, H. Suga, Y. Isogami, H. Tamura and X. Shi: Bull. Chem. Soc. Jpn. 65 2998 (1992).
10. A. Hassner and B. Fischer: Tetrahedron 45 3535 (1989).
11. H. Suga and T. Ibata: Chem. Lett. 1221 (1991).
12. H. Suga, X. Shi and T. Ibata: Bull. Chem. Soc. Jpn. 71 1231 (1998).
13. E. Vedejs and S. Fields: J. Org. Chem. 53 4663 (1988).
14. Kondrat'eva also studied this type of reaction with olefins. G. Ya. Kondrat'eva, M. A. Aitzhanova and V. S. Bogdanov: Izv. Akad. Nauk SSSR, Ser. Khim. 1313 (1979).
15. V. S. Bogdanov, G. Ya. Kondrat'eva and M. A. Aitzhanova: Izv. Akad. Nauk SSSR, Ser. Khim. 1017 (1980).
16. Saalfrank also studied this type of reaction with olefins. R. W. Saalfrank, C.-J. Lurz, J. Hassa, D. Danion and L. Toupet: Chem. Ber. 124 595 (1991).
17. Hassner reported the intramolecular reaction. A. Hassner and B. Fischer: J. Org. Chem. 56 3419 (1991).
18. Y. Ito, M. Sawamura and T. Hayashi: J. Am. Chem. Soc. 108 6405 (1986).
19. Y. Ito, M. Sawamura and T. Hayashi: Tetrahedron Lett. 28 6215 (1987).
20. Y. Ito, M. Sawamura and T. Hayashi: Tetrahedron Lett. 29 239 (1988).
21. Y. Ito, M. Sawamura, E. Shirakawa, K. Hayashizaki and T. Hayashi: Tetrahedron Lett. 29 235 (1988).
22. Y. Ito, M. Sawamura, E. Shirakawa, K. Hayashizaki and T. Hayashi: Tetrahedron 44 5253 (1988).
23. H. Suga, X. Shi and T. Ibata: Chem. Lett. 1673 (1994).
24. H. Suga, X. Shi, H. Fujieda and T. Ibata: Tetrahedron Lett. 32 6911 (1991).
25. H. Suga, X. Shi and T. Ibata: J. Org. Chem. 58 7397 (1993).
26. K. Maruoka, T. Itoh and H. Yamamoto: J. Am. Chem,. Soc. 107 4573 (1985).
27. K. Maruoka, M. Sakurai and H. Yamamoto: Tetrahedron Lett. 26 3853 (1985).
28. K. Maruoka, T. Itoh, M. Sakurai, K. Nonoshita and H. Yamamoto: J. Am. Chem. Soc. 110 3588 (1988).
29. K. Maruoka, Y. Araki and H. Yamamoto: J. Am. Chem. Soc. 110 2650 (1988).
30. K. Maruoka, K. Nonoshita, H. Banno and H. Yamamoto: J. Am. Chem. Soc. 110 7922 (1988).
31. K. Maruoka, T. Itoh, T. Shirasaka and H. Yamamoto: J. Am. Chem. Soc. 110 310 (1988).
32. K. Maruoka, Y. Hoshino, T. Shirasaka and H. Yamamoto: Tetrahedron Lett. 29 3967 (1988).
33. K. Nonoshita, H. Banno, K. Maruoka and H. Yamamoto: J. Am. Chem. Soc. 112 316 (1990).
34. K. Maruoka, T. Itoh, M. Sakurai, K. Nonoshita and H. Yamamoto: J. Am. Chem. Soc. 112 7791 (1990).
35. H. Suga, K. Ikai and T. Ibata: Tetrahedron Lett. 39 869 (1998).
36. H. Suga, K. Ikai and T. Ibata: J. Org. Chem. 64 7040 (1999).
37. The gold(I)-catalyzed asymmetric aldol reaction of methyl isocyanoacetate with penta- and tetrafluorobenzaldehydes showed cis-selectivity (cis : trans = 63 : 37 - 62 : 38) with high enantioselectivity (86% ee - 90% ee): V. A. Soloshonok and T. Hayashi: Tetrahedron Lett. 35 2713 (1994).
38. H. Suga, H. Fujieda, Y. Hirotsu and T. Ibata: J. Org. Chem. 59 3359 (1994).
39. X. Shi, T. Ibata, H. Suga and K. Matsumoto: Bull. Chem. Soc. Jpn. 65 3315 (1992).