Asymmetric hetero Diels-Alder reaction catalyzed by chiral cationic palladium(II) and platinum(II) complexes

Journal of Organic Chemistry

Volumn 64, Issue 23, 1999, Pages 8660-8667

  Oi, Shuichi ^a   Terada, Eiji ^a   Ohuchi, Kazuei ^a   Kato, Tomoko ^a   Tachibana, Yukari ^a   Inoue, Yoshio ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKADIENE; GLYOXAL; PALLADIUM COMPLEX; PLATINUM COMPLEX;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; COMPLEX FORMATION; ORGANIC CHEMISTRY;

EID: 0033550290     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9906680     Document Type: Article

References (48)

1. For reviews, see: (a) Bednarski, M. D.; Lyssikatos, J. P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 2, p 661-706. (b) Boger, D. L.; Weinreb, S. M. In Hetero Diels-Alder Methodology in Organic Synthesis; Blomquist, A. T., Wasserman, H., Eds.; Academic Press: San Diego, 1987; Vol. 47.
2. For reviews, see: (a) Bednarski, M. D.; Lyssikatos, J. P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 2, p 661-706. (b) Boger, D. L.; Weinreb, S. M. In Hetero Diels-Alder Methodology in Organic Synthesis; Blomquist, A. T., Wasserman, H., Eds.; Academic Press: San Diego, 1987; Vol. 47.
3. (a) Bednarsky, M.; Maring, C.; Danishefsky, S. Tetrahedron Lett. 1983, 24, 3451.
4. (b) Bednarsky, M.; Danishefsky, S. J. Am. Chem. Soc. 1986, 108, 7060.
5. (c) Maruoka, K.; Itoh, T.; Shirasaka, T.; Yamamoto, H. J. Am. Chem. Soc. 1988, 110, 310.
6. (d) Faller, J. W.; Smart, C. J. Tetrahedron Lett. 1989, 30, 1189.
7. (e) Togni, A. Organometallics 1990, 9, 3106.
8. (f) Corey, E. J.; Cywin, C. L.; Roper, T. D. Tetrahedron Lett. 1992, 33, 6907.
9. (g) Gao, Q.; Maruyama, T.; Mouri, M.; Yamamoto, H. J. Org. Chem. 1992, 57, 1951.
10. (h) Gao, Q.; Ishihara, K.; Maruyama, T.; Mouri, M.; Yamamoto, H. Tetrahedron 1994, 50, 979.
11. (i) Motoyama, Y.; Mikami, K. J. Chem. Soc., Chem. Commun. 1994, 1563.
12. (j) Keck, G. E.; Li, X.-Y.; Krishnamurthy, D. J. Org. Chem. 1995, 60, 5998.
13. (k) Ghosh, A. K.; Mathivanan, P.; Cappiello, J.; Krishnan, K. Tetrahedron: Asymmetry 1996, 7, 2165.
14. (l) Ghosh, A. K.; Mathivanan, P.; Cappiello, J.Tetrahedron Lett. 1997, 38, 2427.
15. (m) Matsukawa, S.; Mikami, K. Tetrahedron: Asymmetry 1997, 8, 815.
16. (n) Schaus, S. E.; Brånalt, J.; Jacobsen, E. N. J. Org. Chem. 1998, 63, 403.
17. Terada, M.; Mikami, K.; Nakai, T. Tetrahedron Lett. 1991, 32, 935.
18. (a) Johannsen, M.; Jørgensen, K. A. J. Org. Chem. 1995, 60, 5757.
19. (b) Johannsen, M.; Jørgensen, K. A. Tetrahedron 1996, 52, 7321.
20. (c) Johannsen, M.; Jørgensen, K. A. J. Chem. Soc., Perkin Trans. 2 1997, 1183.
21. (d) Yao, S.; Johannsen, M.; Hazell, R. G.; Jørgensen, K. A. J. Org. Chem. 1998, 63, 118.
22. Yao, S.; Johannsen, M.; Jørgensen, K. A. J. Chem. Soc., Perkin Trans. 1 1997, 2345.
23. Graven, A.; Johannsen, M.; Jørgensen, K. A. Chem. Commun. 1996, 2373.
24. (a) Evans, D. A.; Miller, S. J.; Lectka, T. J. Am. Chem. Soc. 1993, 115, 6460.
25. (b) Evans, D. A.; Lectka, T.; Miller, S. J. Tetrahedron Lett. 1993, 34, 7027.
26. (c) Evans, D. A.; Murry, J. A.; von Matt, P.; Norcross, R. D.; Miller, S. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 798.
27. (d) Sagasser, I.; Helmchen, G. Tetrahedron Lett. 1998, 39, 261.
28. (a) Davies, D. L.; Fawcett, J.; Garratt, S. A.; Russell, D. R. Chem. Commun. 1997, 1351.
29. (b) Carmona, D.; Cativiela, C.; Elipe, S.; Lahoz, F. J.; Lamata, M. P.; Lopez-Ram de Víu, M. P.; Oro, L. A.; Vega, C.; Viguri, F. Chem. Commun. 1997, 2351.
30. Odenkilk, W.; Rheingold, A. L.; Bosnich, B. J. Am. Chem. Soc. 1992, 114, 6392.
31. Davenport, A. J.; Davies, D. L.; Fawcett, J.; Garratt, S. A.; Lad, L.; Russell, D. R. Chem. Commun. 1997, 2347.
32. Kanemasa, S.; Oderaotoshi, Y.; Sakaguchi, S.; Yamamoto, H.; Tanaka, J.; Wada, E.; Curran, D. P. J. Am. Chem. Soc. 1998, 120, 3074.
33. Oi, S.; Kashiwagi, K.; Terada, E.; Ohuchi, K.; Inoue, Y. Tetrahedron Lett. 1996, 37, 6351.
34. Oi, S.; Kashiwagi, K.; Inoue, Y. Tetrahedron Lett. 1998, 39, 6253.
35. (a) Sodeoka, M.; Ohrai, K.; Shibasaki, M. J. Org. Chem. 1995, 60, 2648.
36. (b) Sodeoka, M.; Tokunoh, E.; Miyazaki, F.; Hagiwara, E.; Shibasaki, M. Synlett 1997, 463.
37. (a) Hagiwara, E.; Fujii, A.; Sodeoka, M. J. Am. Chem. Soc. 1998, 120, 2474.
38. (b) Ferraris, D.; Young, B.; Dudding, T.; Lectka, T. J. Am. Chem. Soc. 1998, 120, 4548.
39. (a) Mikami, K.; Terada, M.; Nakai, T. J. Am. Chem. Soc. 1990, 112, 3949.
40. (b) Mikami, K.; Motoyama, Y.; Terada, M. J. Am. Chem. Soc. 1994, 116, 2812.
41. Larson, E. R.; Danishefsky, S. J. Am. Chem. Soc. 1982, 104, 6458.
42. (a) Miyano, S.; Okada, S.; Hotta, H.; Takeda, M.; Kabuto, C.; Hashimoto, H. Bull. Chem. Soc. Jpn. 1989, 62, 1528.
43. (b) Miyano, S.; Okada, S.; Hotta, H.; Takeda, M.; Suzuki, T.; Kabuto, C.; Yasuhara, F. Bull. Chem. Soc. Jpn. 1989, 62, 3886.
44. (c) Hattori, T.; Hotta, H.; Suzuki, T.; Miyano, S. Bull. Chem. Soc. Jpn. 1993, 66, 613.
45. Ozawa, F.; Kubo, A.; Matsumoto, Y.; Hayashi, T. Organometallics 1993, 12, 4188.
46. Trost, B. M.; Romero, D. L.; Rise, F. J. Am. Chem. Soc. 1994, 116, 4268.
47. Riley, H. A.; Gray, A. R. In Organic Syntheses; Blatt, A. H., Ed.; John Wiley & Sons: New York, 1943; Collect. Vol. 2, p 509.
48. Kelly, T. R.; Schmidt, T. E.; Haggerty, J. G. Synthesis 1972, 544.