A novel, chiral Lewis acid-induced enantioselective hetero Diels-Alder reaction of a thiabutadiene

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 20, 1997, Pages 2957-2959

  Saito, Takao ^a   Takekawa, Kayoko ^a   Nishimura, Jun Ichi ^a   Kawamura, Mikako ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33748661307     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/a703590j     Document Type: Article

References (48)

1. H. Waldmann, Synthesis, 1994, 535;
2. J. Streith and A. Defoin, Synthesis, 1994, 1107;
3. C. Kibayashi and S. Aoyagi, Synlett, 1995, 873;
4. H. B. Kagan and O. Riant, Chem. Rev., 1992, 92, 1007;
5. T. Oh and M. Reilly, Org. Prep. Proced. Int., 1994, 26, 129;
6. U. Pindur, G. Lutz and C. Otto, Chem. Rev., 1993, 93, 741;
7. T. Kametani and S. Hibino, Adv. Heterocycl. Chem., 1987, 42, 245;
8. L. F. Tietze and U. Beifuss, Angew. Chem., Int. Ed. Engl., 1993, 32, 131;
9. R. R. Schmidt, Acc. Chem. Res., 1986, 19, 250;
10. M. D. Bednarski and J. P. Lyssikatos, in Comprehensive Organic Synthesis, ed. B. M. Trost, I. Fleming and L. A. Paquette, Pergamon, Oxford, 1991, vol. 2, p. 661;
11. S. M. Weinreb, in Comprehensive Organic Synthesis, ed. B. M. Trost, I. Fleming and L. A. Paquette, Pergamon, Oxford, 1991, vol. 5, p. 401;
12. D. L. Boger, in Comprehensive Organic Synthesis, ed. B. M. Trost, I. Fleming and L. A. Paquette, Pergamon, Oxford, 1991, vol. 5, p. 451.
13. For recent reports on asymmetric hetero Diels-Alder reactions: J. Mulzer and F. Meyer, Tetrahedron Lett., 1995, 36, 3503;
14. K. Mikami, O. Kotera, Y. Motoyama and H. Sakaguchi, Synlett, 1995, 975;
15. A. Graven, M. Johannsen and K. A. Jorgensen, Chem. Commun., 1996, 2373;
16. R. Lock and H. Waldmann, Tetrahedron Lett., 1996, 37, 2753;
17. H. Ishitani and S. Kobayashi, Tetrahedron Lett., 1996, 37, 7359;
18. R. Badorrey, C. Cativiela, M: D. Díaz-de-Villegas and J. A. Gálvez, Tetrahedron Lett., 1997, 38, 2547;
19. S. E. Denmark, A. R. Hurd and H. J. Sacha, J. Org. Chem., 1997, 62, 1668;
20. S. E. Denmark and A. Thorarensen, J. Am. Chem. Soc., 1997, 119, 125;
21. S. E. Denmark and L. R. Marcin, J. Org. Chem., 1997, 62, 1675.
22. For asymmetric hetero Diels-Alder reaction with nitroso dienophiles: M. Naruse, S. Aoyagi and C. Kibayashi, J. Org. Chem., 1994, 59, 1358;
23. J.-B. Behr, A. Defoin, J. Pires, J. Streith, L. Macko and M. Zehnder, Tetrahedron, 1996, 52, 3283;
24. A. R. Ritter and M. J. Miller, J. Org. Chem., 1994, 59, 4602.
25. For asymmetric hetero Diels-Alder reaction with nitroso dienes: T. Arnold, B. Orschel and H.-V. Reissig, Angew. Chem., Int. Ed. Engl., 1992, 31, 1033.
26. For asymmetric hetero Diels-Alder reaction with nitro dienes: S. E. Denmark and M. E. Schnute, J. Org. Chem., 1994, 59, 4576.
27. For asymmetric hetero Diels-Alder reaction with N-sulfinylamine dienophiles: S. M. Weinreb, Acc. Chem. Res., 1988, 21, 313.
28. For asymmetric hetero Diels-Alder reaction with thiocarbonyl dienophiles: E. Vedjes, J. S. Stults and R. G. Wilde, J. Am. Chem. Soc., 1988, 110, 5452;
29. G. W. Kirby and A. D. Sclare, J. Chem. Soc., Perkin Trans. 1, 1991, 2329;
30. B. F. Bonini, G. Mazzanti, P. Zani and G. Maccagnani, J. Chem. Soc., Chem. Commun., 1988, 365;
31. P. A. T. W. Porskamp, R. C. Haltiwanger and B. Zwanenburg, Tetrahedron Lett., 1983, 24, 2035;
32. L. A. G. M. van den Broek, P. A. T. W. Porskamp, R. C. Haltiwanger and B. Zwanenburg, J. Org. Chem., 1984, 49, 1691;
33. T. Takahashi, N. Kurose and T. Koizumi, Heterocycles, 1993, 36, 1601.
34. S. Motoki, T. Saito, T. Karakasa, H. Kato, T. Matsushita and S. Hayashibe, J. Chem. Soc., Perkin Trans. 1, 1991, 2281;
35. T. Saito, H. Fujii, S. Hayashibe, T. Matsushita, H. Kato and K. Kobayashi, J. Chem. Soc., Perkin Trans. 1, 1996, 1897.
36. T. Saito, T. Karakasa, H. Fujii, E. Furuno, H. Suda and K. Kobayashi, J. Chem. Soc., Perkin Trans. 1, 1994, 1359.
37. T. Saito, M. Kawamura and J. Nishimura, Tetrahedron Lett., 1997, 38, 3231.
38. T. Saito, H. Suda, M. Kawamura, J. Nishimura and A. Yamaya, Tetrahedron Lett., 1997, 38, 6035.
39. A. Marchand, D. Mauger, A. Guingant and J.-P. Pradère, Tetrahedron: Asymmetry, 1995, 6, 853.
40. A. S. Bell, C. W. G. Fishwick and J. E. Reed, Tetrahedron Lett., 1996, 37, 123.
41. D. A. Evans, K. T. Chapman and J. Bisaha, J. Am. Chem. Soc., 1988, 110, 1238.
42. D. A. Evans, T. Lectka and S. J. Miller, Tetrahedron Lett., 1993, 34, 7027.
43. Z. Li, K. R. Conser and E. N. Jacobsen, J. Am. Chem. Soc., 1993, 115, 5326.
44. K. Narasaka, N. Iwasawa, M. Inoue, T. Yamada, M. Nakashima and J. Sugimori, J. Am. Chem. Soc., 1989, 111, 5340;
45. K. Narasaka, Synthesis, 1991, 1;
46. D. Seebach, R. Dahinden, R. E. Marti, A. K. Beck, D. A. Plattner and N. M. Kühnle, J. Org. Chem., 1995, 60, 1788;
47. K. V. Gothelf and K. A. Jørgensen, J. Org. Chem., 1995, 60, 6847;
48. C. Haase, C. R. Sarko and M. DiMare, J. Org. Chem., 1995, 60, 1777.