Catalytic asymmetric epoxidation of α, β-unsaturated carbonyl compounds

Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry

Volumn 60, Issue 2, 2002, Pages 94-105

  Nemoto, Tetsuhiro ^a   Ohshima, Takashi ^a   Shibasaki, Masakatsu ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

Catalytic asymmetric epoxidation; Chiral ligand metal peroxide complex; Phase transfer catalyst; Polyamino acid catalyst; Weitz Scheffer type reaction; , epoxy ketones; , unsaturated carboxylic acid derivatives

Indexed keywords

AMINO ACIDS; CARBOXYLIC ACIDS; CATALYSIS; CATALYSTS; DERIVATIVES; EPOXY RESINS; KETONES; OXIDATION; SYNTHESIS (CHEMICAL);

CATALYTIC ASYMMETRIC EPOXIDATION REACTIONS; PHASE-TRANSFER CATALYSTS;

AROMATIC HYDROCARBONS;

EID: 0036486779     PISSN: 00379980     EISSN: None     Source Type: Journal    
DOI: 10.5059/yukigoseikyokaishi.60.94     Document Type: Review

References (76)

1. (a) I. Ojima, Catalytic Asymmetric Synthesis, 2nd ed" Wiley, New York, 2000.
2. (b) E.N. Jacobsen, M.H. Wu, "Comprehensive Asymmetric Catalysis" E.N. Jacobsen, A. Pfaltz, H. Yamamoto, Eds., Springer, New York, 1999, p 649.
3. (c) R. Noyori, "Asymmetric Catalysis In Organic Synthesis" John Wiley and Sons, Inc., New York, 1994.
4. (a) K. Katsuki, K.B. Sharpless, J. Am. Chem. Soc., 102, 5974 (1980).
5. (b) R.M. Hanson, K.B. Sharpless, J. Org. Chem., 51, 1992 (1986).
6. (a) W. Zhang, J.L. Loebach, S.R. Wilson, E.N. Jacobsen, J. Am. Chem. Soc., 112, 2801 (1990).
7. (b) R. Irie, K. Noda, Y. Ito, N. Matsumoto, T. Katsuki, Tetrahedron Lett., 31, 7345 (1990).
8. (c) T. Yamada, K. Imagawa, T. Nagata, T. Mukaiyama, Chem. Lett., 1992, 2231.
9. (a) R. Curci, M. Fiorentino, M.R. Serio; J. Chem. Soc., Chem. Commun., 1984, 155.
10. (b) Z.-C. Wang, Y. Shi, J. Org. Chem., 62, 8622 (1997).
11. (c) D. Yang, M.-K. Wong, Y.-C. Yip, X.-C. Wang, M.-W. Tang, Y.-C. Zheng, K.-K. Cheung, J. Am. Chem. Soc., 120, 5943 (1998).
12. M.J. Porter, J. Skidmore, Chem. Commun., 2000, 1215.
13. A. Nelson, Angew. Chem. Int. Ed. Engl., 38, 1583 (1999).
14. R. Helder, J.C. Hummelen, R.W.P.M. Laane, J.S. Wiering, H. Wynberg, Tetrahedron Lett., 1976, 1831.
15. Y. Harigaya, H. Yamaguchi, M. Onda, Heterocycles, 15, 183 (1981).
16. J.P. Mazaleyrat, Tetrahedron Lett., 24, 1243 (1983).
17. N. Baba, J. Oda, M. Kawaguchi, Agric. Biol. Chem, 50, 3113 (1986).
18. M. Shi, Y. Masaki, J. Chem. Res. (S), 1994, 250.
19. (a) B. Lygo, P.G. Wainwright, Tetrahedron Lett., 39, 1599 (1998).
20. B. Lygo, D.C.M. To, ibid., 42, 1343 (2001).
21. S. Arai, H. Tsuge, T. Shioiri, Tetrahedron Lett., 39, 7563 (1998).
22. E.J. Corey, F.-Y. Zhang, Org. Lett., 1, 1287 (1999).
23. G. Macdonald, L. Alcaraz, N.J. Lewis, R.J.K. Taylor, Tetrahedron Lett., 39, 5433 (1998).
24. M.J. Porter, S.M. Roberts, J. Skidmore, Bioorg. Med. Chem., 7, 2145 (1999).
25. (a) S. Juliá, J. Masana, J.C. Vega, Angew. Chem. Int. Ed. Engl., 19, 929 (1980).
26. (a) S. Banfi, S. Colonna, H. Molinari, S. Juliá, J. Guixer, Tetrahedron, 40, 5207 (1984) and references therein.
27. M.E. Lasterra-Sánchez, U. Felfer, P. Mayon, S.M. Roberts, S.R. Thornton, C.J. Todd, J. Chem. Soc., Perkin Trans. 1, 1996, 343.
28. P.A. Bentley, S. Bergeron, M.W. Cappi, D.E. Hibbs, M.B. Hursthouse, T.C. Nugent, R. Pulido, S.M. Roberts, L.E. Wu, Chem. Commun., 1997, 739.
29. J.V. Allen, K.-H. Drauz, T.P. Geller, S.M. Roberts, J. Skidmore, Tetrahedron Lett., 40, 5417 (1999).
30. J.V. Allen, S. Bergeron, M.J. Griffiths, S. Mukherjee, S.M. Roberts, N.M. Williamson, L.E. Wu, J. Chem. Soc., Perkin Trans. 1, 1998, 3171.
31. (a) S. Itsuno, M. Sakakura, K. Ito, J. Org. Chem., 55, 6047 (1990).
32. (b) M.W. Cappi, W.-P. Chen, R.W. Flood, Y.-W. Liao, S.M. Roberts, J. Skidmore, J.A. Smith, N.M. Williamson, Chem. Commun., 1998, 1159.
33. (c) T. Geller, S.M. Roberts, J. Chem. Soc., Perkin Trans. 1, 1999, 1397.
34. (a) R. Takagi, A. Shiraki, T. Manabe, S. Kojima, K. Ohkata, Chem. Lett., 2000, 366.
35. (b) R.W. Flood, T.P. Geller, S.A. Petty, S.M. Roberts, J. Skidmore, M. Volk, Org. Lett., 3, 683 (2001).
36. P.A. Bentley, M.W. Cappi, R.W. Flood, S.M. Roberts, J.A. Smith, Tetrahedron Lett., 39, 9297 (1998).
37. (a) J.R. Flisak, K.J. Gombatz, M.M. Holmes, A.A. Jarmas, I. Lantos, W.L. Mendelson, V.J. Novack, J.J. Remich, L. Snyder, J. Org. Chem., 58, 6247 (1993).
38. (a) L. Carde, H. Davies, T.P. Geller, S.M. Roberts, Tetrahedron Lett., 40, 5421 (1999).
39. (a) H. van Rensburg, P.S. van Heerden, B.C.B. Bezuidenhoudt, D. Ferreira, Tetrahedron, 53, 14141 (1997).
40. (b) R.J.J. Nel, P.S. van Heerden, H. van Rensburg, D. Ferreira, Tetrahedron Lett., 39, 5623 (1997).
41. P.C. Ray, S.M. Roberts, J. Chem. Soc., Perkin Trans. 1, 2001, 149.
42. C. Baccin, A. Gusso, F. Pinna, G. Strukul, Organometallics, 14, 1161 (1995).
43. (a) D. Enders, J. Zhu, G. Raabe, Angew. Chem. Int. Ed. Engl., 35, 1725 (1996).
44. (b) H.-B. Yu, X.-F. Zheng, Z.-M. Lin, Q.-S. Hu, W.-S. Hung, L. Pu, J. Org. Chem., 64. 8149 (1999).
45. C.L. Elston, R.F.W. Jackson, S.J.F. MacDonald, P.J. Murray, Angew. Chem. Int. Ed. Engl., 36, 410 (1997).
46. (a) M. Bougauchi, S. Watanabe, T. Arai, H. Sasai, M. Shibasaki, J. Am. Chem. Soc., 119, 2329 (1997).
47. (b) S. Watanabe, Y. Kobayashi, T. Arai, H. Sasai, M. Bougauchi, M. Shibasaki, Tetrahedron Lett., 39, 7353 (1998).
48. (c) K. Daikai, M. Kamaura, J. Inanaga, ibid., 39, 7321 (1998).
49. (d) T, Nemoto, T. Ohshima, K. Yamaguchi, M. Shibasaki, J. Am. Chem. Soc., 123, 2725 (2001).
50. (e) S. Watanabe, T. Arai, H. Sasai, M. Bougauchi, M. Shibasaki, J. Org. Chem., 63. 8090 (1998).
51. (a) H. Sasai, T. Arai, M. Shibasaki, J. Am. Chem. Soc., 116, 1571 (1994).
52. (b) H. Sasai, T. Arai, Y. Satou, K.N. Houk, M. Shibasaki, ibid., 117, 6194 (1995).
53. (c) T. Arai, H. Sasai, K. Aoe, K. Okamura, T. Date, M. Shibsaki, Angew. Chem. Int. Ed. Engl., 35, 104 (1996).
54. (d) T. Arai, Y.M.A. Yamada, N. Yamamoto, H. Sasai, M. Shibasaki, Chem. Eur. J., 2, 1368 (1996).
55. (e) Y.-S. Kim, S. Matsunaga, J. Das, A. Sekine, T. Ohshima, M. Shibasaki, J. Am. Chem. Soc., 122, 6506 (2000).
56. (f) S. Matsunaga, T. Ohshima, M. Shibasaki, Tetrahedron Lett., 41, 8473 (2000).
57. (a) K. Yamada, T. Arai, H. Sasai, M. Shibasaki, J. Org. Chem., 63. 3666 (1998).
58. (b) T. Nemoto, T. Ohshima, M. Shibasaki, Tetrahedron Lett., 41, 9569 (2000).
59. M. Frohn, Y. Shi, Synthesis, 2000, 1979.
60. Z.-X. Wang, S. M. Miller, O.P. Anderson, Y. Shi, J. Org. Chem., 64, 6443 (1999).
61. W. Adam, P.B. Rao, H.-G. Degen, C.R. Saha-Möller, J. Am. Chem. Soc., 122, 5654 (2000).
62. S. Colonna, N. Gaggero, M. Spadoni, L. Casella, G. Carrea, P. Pasta, Tetrahedron, 44, 5169 (1988) and references therein.
63. A. Kumar, V. Bhakuni, Tetrahedron Lett., 37, 4751 (1996).
64. (a) Y. Hu, A. Harada, S. Takahashi, Synth. Commun., 18, 1607 (1988).
65. (b) S. Colonna, A. Manfredi, R. Annunziata, N. Gaggero, L. Casella, J. Org. Chem., 55, 5862 (1990).
66. R. Imashiro, T. Kuroda, Tetrahedron Lett., 42, 1313 (2001) and references therein.
67. B. M. Adger, J. V. Barkley, S. Bergeron, M. W. Cappi, B. E. Flowerdew, M. P. Jackson, R. MaCague, T. C. Nugent, S. M. Roberts, J. Chem. Soc., Perkin Trans. 1, 1997, 3501.
68. R. Takagi, J. Kimura, Y. Shinohara, Y. Ohba, K. Takezono, Y. Hiraga, S. Kojima, K. Ohkata, J. Chem. Soc., Perkin Trans. 1, 1998, 689.
69. R. Giuliana, R. Giovanna, B. Carlo, J. Org. Chem., 61, 3557 (1996).
70. (a) E.N. Jacobsen, W. Zhang, A.R. Muci, J.R. Ecker, L. Deng, J. Am. Chem. Soc., 113, 7063 (1991).
71. (b) E.N. Jacobsen, L. Deng, Y. Furukawa, L.E. Martínez, Tetrahedron, 50, 4323 (1994).
72. A. Armstrong, B.R. Hayter, Chem. Commun., 1998, 621.
73. A. Solladié-Cavalio, L. Bouérat, Org. Lett., 2, 3531 (2000).
74. T. Nemoto, T. Ohshima, M. Shibasaki, J. Am. Chem. Soc., 123, 9474 (2001).
75. E.N. Prabhakaran, J.P. Nandy, S. Shukla, J. Iqbal, Tetrahedron Lett., 333, 42 (2001).