The Juliä-Colonna type asymmetric epoxidation reaction catalyzed by soluble Oligo-L-leucines containing an α-aminoisobutyric acid residue: Importance of helical structure of the catalyst on asymmetric induction

Chemistry Letters

Volumn , Issue 4, 2000, Pages 366-367

  Takagi, Ryukichi ^a   Shiraki, Akiko ^a   Manabe, Toshiki ^a   Kojima, Satoshi ^a   Ohkata, Katsuo ^a  

^a HIROSHIMA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0034358478     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2000.366     Document Type: Article

References (39)

1. a) M. Bartok and K. L. Lang, "The Chemistry of Ethers, Crown Ethers, Hydroxyl Groups and Their Sulphur Analogs, Supplement E," ed by S. Patai, John Wiley, New York (1980) vol. 2, p. 609.
2. b) A. S. Rao, S. K. Paknikar, and J. G. Kirtane, Tetrahedron, 39, 2323 (1983).
3. c) J. G. Smith, Synthesis, 1984, 629.
4. d) E. G. Lewars, in "Comprehensive Heterocyclic Chemistry," ed by A. R. Katritzky and C. W. Rees, Pergamon, Oxford (1984), vol. 7, p. 95.
5. e) I. Erden, in "Comprehensive Heterocyclic Chemistry II," ed by A. Padwa, Elsevier, Oxford (1996), vol. 1 A, p. 97.
6. a) T. Katsuki and K. B. Sharpless, J. Am. Chem. Soc., 102, 5874 (1980).
7. b) W. Zhang, J. L. Loebach, S. R. Wilson, and E. N. Jacobsen, J. Am. Chem. Soc., 112, 2801 (1990).
8. c) R. Irie, K. Noda, Y. Ito, N. Matsumoto, and T. Katsuki, Tetrahedron Lett., 31, 7345 (1990).
9. d) S. Juliá, J. Masana, and J. C. Vega, Angew. Chem., Int. Ed. Engl., 19, 929 (1980).
10. e) D. Yang, Y.-C. Yip, M.-W. Tang. M-K. Wong, J.-H. Zheng, and K.-K. Cheung, J. Am. Chem. Soc, 118, 491 (1996).
11. f) Y. Tu, Z.-X. Wang, and Y. Shi, J. Am. Chem. Soc., 118, 9806 (1996).
12. g) D. Enders, J. Zhu, and G. Raabe, Angew. Chem., Int. Ed. Engl., 35, 1725 (1996).
13. h) M. Bougauchi, S. Watanabe, T. Arai, H. Sasaki, and M. Shibasaki, J. Am. Chem. Soc., 119, 2329 (1997).
14. i) C. L. Elston, R. F. W. Jackson, S. J. F. MacDonald, and P. J. Murray, Angew. Chem., Int. Ed. Engl., 36, 410 (1997).
15. j) B. Lygo and P. G. Wainwright, Tetrahedron Lett., 39, 1599 (1998).
16. k) S. Watanabe, T. Arai, H. Sasaki, M. Bougauchi, and M. Shibasaki, J. Org. Chem., 63, 8090 (1998).
17. For reviews on Juliá-Colonna epoxidalion see: a) M. E. Lasterra-Sanchez and S. M. Roberts, Curr. Org. Chem., 1, 187 (1997).
18. b) S. Ebrahim and M. Wills, Tetrahedron: Asymmetry, 8, 3163 (1997).
19. c) L. Pu, Tetrahedron: Asymmetry, 9, 1457 (1998).
20. a) J. R. Flisak, K. J. Gombatz, M. M. Holmes, A. A. Jamas, I. Lantos, W. L. Mendelson, V. J. Navack, J. J. Remich, and L. Snyder, J. Org. Chem., 58, 6247 (1993).
21. b) R. J. J. Nel, P. S. van Heerden, H. van Rensburg, and D. Ferreira Tetrahedron Lett., 39, 5623 (1998).
22. c) B. M. Adger, J. V. Barkley, S. Bergeron, M. W. Cappi, B. E. Flowerdew, M. P. Jackson, R. McCague, T. C. Nugent, and S. M. Roberts, J. Chem. Soc., Perkin Trans. 1, 1997, 3501.
23. d) M. W. Cappi, W.-P. Chen, R. W. Flood, Y.-W. Liao, S. M. Roberts, J. Skidmore, J. A. Smith, and N. M. Williamson, Chem. Commun., 1998, 1159.
24. e) W.-p. Chen and S. M. Roberts, J. Chem. Soc., Perkin Trims. 1, 1999, 1043.
25. a) K. Ohkata, J. Kimura, Y. Shinohara, R. Takagi, and Y. Hiraga, Chem. Commun., 1996, 2411.
26. b) R. Takagi, J. Kimura, Y. Shinohara, Y. Ohba, K. Takezono, Y. Hiraga, S. Kojima, and K. Ohkata, J. Chem. Soc., Perkin Trans. 1, 1998, 689.
27. S. Itsuno, M. Sakakura, and K. Ito, J. Org. Chem., 53, 6047 (1990).
28. P. A. Bentley, M. W. Cappi, R. W. Flood, S. M. Robert, and J. A. Smith, Tetrahedron Lett., 39, 9297 (1998).
29. a) S. Juliá, J. Gulixer, J. Masana, J. Rocas, S. Colonna, R. Annuziata, and H. Molinari, J. Chem. Soc., Perkin Trans. 1, 1982, 1317.
30. b) S. Colonna, H. Molinari, S. Banfi, S. Juliá, J. Masana, and A. Alvarez, Tetrahedron, 39, 1635 (1983).
31. c) S. Banfi, S. Colonna, H. Molinari, S. Juliá, and J. Guixer, Tetrahedron, 40, 5207 (1984).
32. Manuscript in preparation.
33. M. Narita, K. Ishikawa, H. Sugasawa, and M. Doi, Bull. Chem. Soc. Jpn., 58, 1731 (1985).
34. 4 and evaporated. The crude product was purified by preparative TLC (silica gel, petroleum ether : ether = 10: 1 (v/v)]. As the reaction progresses, the turbidity caused by the lowly soluble urea-hydrogen peroxide adduct decreases.
35. 3, solutions: By the same procedure except without catalyst, the racemic epoxide was furnished in 26 and 68% yield, respectively.
36. a) T. Miyazawa and E. J. Blout, J. Am. Chem. Soc., 83, 712 (1961).
37. b) D. F. Kennedy, M. Crisma, C. Toniolo, and D. Chapman, Biochemistry, 30, 6541 (1991).
38. 10-helical conformation, thus implying the presence of this structure: a) M. Manning and R. W. Woody, Biapolymers, 31, 569 (1991).
39. b) C. Toniolo, A. Polese, F. Formaggio, M. Crisma, and J. Kamphuis, J. Am. Chem. Soc., 118, 2744 (1996).