Bisoxazoline and bioxazoline chiral ligands bearing 4-diphenylmethyl shielding substituents. Diels-Alder reaction of cyclopentadiene with 3- acryloyl-2-oxazolidinone catalyzed by the aqua nickel(II) complex

Bulletin of the Chemical Society of Japan

Volumn 73, Issue 3, 2000, Pages 681-687

  Kanemasa, Shuji ^a   Adachi, Kenji ^a   Yamamoto, Hidetoshi ^b   Wada, Eiji ^a  

^a KYUSHU UNIVERSITY   (Japan)

^b YAMAGUCHI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BIPHENYL DERIVATIVE; CYCLOPENTADIENE DERIVATIVE; LIGAND; NICKEL COMPLEX; OXAZOLIDINONE DERIVATIVE; OXAZOLINE DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHIRALITY; COMPLEX FORMATION; OPTICAL RESOLUTION; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033932848     PISSN: 00092673     EISSN: None     Source Type: Journal    
DOI: 10.1246/bcsj.73.681     Document Type: Article

References (46)

1. S. Kanemasa and K. Onimura, Tetrahedron, 48, 8631 (1992).
2. S. Kanemasa and K. Onimura, Tetrahedron, 48, 8645 (1992).
3. S. Kanemasa, H. Suenaga, and K. Onimura, J. Org. Chem., 59, 6949 (1994).
4. S. Kanemasa, M. Nomura, S. Yoshinaga, and H. Yamamoto, Tetrahedron, 51, 10463 (1995).
5. a) D. Muller, G. Umbricht, B. Weber, and A. Pfaltz, Helv. Chim. Acta, 74, 232 (1991).
6. b) Y. Ukaji, M. Miyamoto, M. Mikuni, S. Takeuchi, and K. Inomata, Bull. Chem. Soc. Jpn., 69, 735 (1996).
7. As a recent review: A. K. Ghosh, M. Mackiarajan, and J. Cappiello, Tetrahedron Asymm., 9, 1 (1998).
8. a) D. A. Evans, J. A. Murry, and M. C. Kozlowski, J. Am. Chem. Soc., 118, 5814 (1996).
9. b) D. A. Evans, M. C. Kozlowski, and J. S. Tedrow, Tetrahedron Lett., 37, 7481 (1996).
10. c) D. A. Evans, M. C. Kozlowski, C. S. Burgey, and D. W. C. MacMillan, J. Am. Chem. Soc., 119, 7893 (1997).
11. d) D. A. Evans, T. Rovis, M. C. Kozlowski, and J. S. Tedrow, J. Am. Chem. Soc., 121, 1994 (1999).
12. a) H. Nishiyama, S. Yamaguchi, S.-B. Park, and K. Itoh, Tetrahedron Asymm., 4, 143 (1993).
13. b) H. Nagashima, T. Ueda, H. Nishiyama, and K. Itoh, Chem. Lett., 1993, 347.
14. c) H. Nishiyama, Y. Itoh, Y. Sugawara, H. Matsumoto, K. Aoki, and K. Itoh, Bull. Chem. Soc. Jpn., 68, 1247 (1995).
15. d) S.-B. Park, N. Sakata, and H. Nishiyama, Chem. Europ. J., 2, 303 (1996).
16. e) H. Brunner, C. Bluechel, and M. P. Doyle, J. Organomet. Chem., 541, 89 (1997).
17. f) H. Nishiyama, T. Shimada, H. Itoh, H. Sugiyama, and Y. Motoyama, J. Chem. Soc., Chem. Commun., 1997, 1863.
18. g) A. I. Sanchez-Blanco, K. V. Gothelf, and K. A. Jorgensen, Tetrahedron Lett., 38, 7923 (1997).
19. h) A. Yanagisawa, K. Kimura, Y. Nakatsuka, and H. Yamamoto, Synlett., 1998, 958.
20. i) D. A. Evans and J. S. Johnson, J. Am. Chem. Soc., 120, 4895 (1998).
21. j) D. A. Evans, C. S. Burgey, N. A. Paras, T. Vojkovsky, and S. W. Tregay, J. Am. Chem. Soc., 120, 5824 (1998).
22. a) S. Kanemasa, Y. Oderaotoshi, H. Yamamoto, J. Tanaka, E. Wada, and D. P. Curran, J. Org. Chem., 62, 6454 (1997).
23. b) S. Kanemasa, Y. Oderaotoshi, S.-I. Sakaguchi, H. Yamamoto, J. Tanaka, E. Wada, and D. P. Curran, J. Am. Chem. Soc., 120, 3074 (1998).
24. c) S. Kanemasa, Y. Oderaotoshi, and E. Wada, Synth. Org. Chem. Jpn., 56, 368 (1998).
25. d) S. Kanemasa, Y. Oderaotoshi, J. Tanaka, and E. Wada, Tetrahedron Lett., 39, 7521 (1998).
26. e) S. Kanemasa, Y. Oderaotoshi, J. Tanaka, and E. Wada, J. Am. Chem. Soc., 120, 12355 (1998).
27. E. Pierson, M. Giella, and M. Tishler, J. Am. Chem. Soc., 70, 1450 (1948).
28. Melting point of oxalic acid is 104 °C so that the reaction mixture melts at the reaction temperature applied.
29. A. M. Koskinen, H. Hassila, V. T. Myllymaki, and K. Rissanen, Tetrahedron Lett., 36, 5619 (1995).
30. D. A. Evans, S. J. Miller, and T. Lectka, J. Am. Chem. Soc., 115, 6460 (1993).
31. E. J. Corey, N. Imai, and H. Zhang, J. Am. Chem. Soc., 113, 728 (1991).
32. E. J. Corey and K. Ishihara, Tetrahedron Lett., 33, 6807 (1992).
33. a) A. S. Gokhale, A. B. E. Minidis, and A. Pfaltz, Tetrahedron Lett., 36, 1831 (1995).
34. b) M. B. Andrus, A. B. Argade, X. Chen, and M. G. Pamment, Tetrahedron Lett., 36, 2945 (1995).
35. c) M. Miura, M. Enna, K. Okuno, and M. Nomura, J. Org. Chem., 60, 4999 (1995).
36. d) M. Johannsen and K. A. Jørgensen, J. Org. Chem., 60, 5757 (1995).
37. e) M. Johannsen, and K. A. Jørgensen, Tetrahedron, 52, 7321 (1996).
38. f) R. Schumacher and H.-U. Reissig, Liebigs Ann., Recl., 521 (1997).
39. g) R. Schumacher, F. Dammast, and H.-U. Reissig, Chem. Europ. J., 3, 614 (1997).
40. h) S. Yao, M. Johannsen, R. G. Hazell, and K. A. Jørgensen, J. Org. Chem., 63, 118 (1998).
41. For the determination of absolute configuration of (S)-15: Ref. 9b.
42. Reversal enantioselectivity of t-butyl vs. phenyl-substituted bisoxazoline-copper(II) complex catalyzed Diels-Alder and ene-reactions: D. A. Evans, J. S. Johnson, C. S. Burgey, and K. R. Campos, Tetrahedron Lett., 40, 2879 (1999).
43. For the nickel(II) complex catalyzed Diels-Alder reactions where square planar transition state geometries have been involved: A. K. Ghosh, H. Cho, and J. Capiello, Tetrahedron Asymm., 9, 3687 (1998).
44. H. G. Chen, V. G. Beylin, M. Marlatt, B. Leya, and O. P. Goel, Tetrahedron Lett., 33, 3293 (1992).
45. a) M. P. Sibi, P. K. Deshpande, A. J. L. Loggia, and J. W. Christensen, Tetrahedron Lett., 36, 8961 (1995).
46. b) H. G. Chen, V. G. Beylin, M. Marlatt, B. Leja, and O. P. Goel, Tetrahedron Lett., 33, 3293 (1992).