α-Sulfenyl-Directed Ring-Opening Reactions of Epoxides. 1. Highly Regio- and Stereoselective Reaction with Organo-Aluminum Reagents and Application to the Synthesis of an Aggregation Pheromone

Bulletin of the Chemical Society of Japan

Volumn 69, Issue 7, 1996, Pages 2095-2105

  Liu, Changqing ^a   Hashimoto, Yukihiko ^a   Kudo, Kazuaki ^a   Saigo, Kazuhiko ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001338438     PISSN: 00092673     EISSN: None     Source Type: Journal    
DOI: 10.1246/bcsj.69.2095     Document Type: Article

References (52)

1. R. A. Johnson and K. B. Sharpless, "Comprehensive Organic Synthesis," ed by B. M. Trost and I. Fleming, Pergamon Press, Oxford (1991), Vol. 7, pp. 389-436; R. M. Hanson, Chem. Rev., 91, 437 (1991); A. Pfenniger, Synthesis, 1986, 89; B. E. Rossitier, "Asymmetric Synthesis," ed by J. D. Morrison, Academic Press, New York (1985), Vol. 5, pp. 193-246; C. H. Behrens and K. B. Sharpless, Aldrichimica Acta, 16, 67 (1983); A. S. Rao, S. K. Paknikar, and J. G. Kirtane, Tetrahedron, 39, 2323 (1983).
2. R. A. Johnson and K. B. Sharpless, "Comprehensive Organic Synthesis," ed by B. M. Trost and I. Fleming, Pergamon Press, Oxford (1991), Vol. 7, pp. 389-436; R. M. Hanson, Chem. Rev., 91, 437 (1991); A. Pfenniger, Synthesis, 1986, 89; B. E. Rossitier, "Asymmetric Synthesis," ed by J. D. Morrison, Academic Press, New York (1985), Vol. 5, pp. 193-246; C. H. Behrens and K. B. Sharpless, Aldrichimica Acta, 16, 67 (1983); A. S. Rao, S. K. Paknikar, and J. G. Kirtane, Tetrahedron, 39, 2323 (1983).
3. R. A. Johnson and K. B. Sharpless, "Comprehensive Organic Synthesis," ed by B. M. Trost and I. Fleming, Pergamon Press, Oxford (1991), Vol. 7, pp. 389-436; R. M. Hanson, Chem. Rev., 91, 437 (1991); A. Pfenniger, Synthesis, 1986, 89; B. E. Rossitier, "Asymmetric Synthesis," ed by J. D. Morrison, Academic Press, New York (1985), Vol. 5, pp. 193-246; C. H. Behrens and K. B. Sharpless, Aldrichimica Acta, 16, 67 (1983); A. S. Rao, S. K. Paknikar, and J. G. Kirtane, Tetrahedron, 39, 2323 (1983).
4. R. A. Johnson and K. B. Sharpless, "Comprehensive Organic Synthesis," ed by B. M. Trost and I. Fleming, Pergamon Press, Oxford (1991), Vol. 7, pp. 389-436; R. M. Hanson, Chem. Rev., 91, 437 (1991); A. Pfenniger, Synthesis, 1986, 89; B. E. Rossitier, "Asymmetric Synthesis," ed by J. D. Morrison, Academic Press, New York (1985), Vol. 5, pp. 193-246; C. H. Behrens and K. B. Sharpless, Aldrichimica Acta, 16, 67 (1983); A. S. Rao, S. K. Paknikar, and J. G. Kirtane, Tetrahedron, 39, 2323 (1983).
5. R. A. Johnson and K. B. Sharpless, "Comprehensive Organic Synthesis," ed by B. M. Trost and I. Fleming, Pergamon Press, Oxford (1991), Vol. 7, pp. 389-436; R. M. Hanson, Chem. Rev., 91, 437 (1991); A. Pfenniger, Synthesis, 1986, 89; B. E. Rossitier, "Asymmetric Synthesis," ed by J. D. Morrison, Academic Press, New York (1985), Vol. 5, pp. 193-246; C. H. Behrens and K. B. Sharpless, Aldrichimica Acta, 16, 67 (1983); A. S. Rao, S. K. Paknikar, and J. G. Kirtane, Tetrahedron, 39, 2323 (1983).
6. R. A. Johnson and K. B. Sharpless, "Comprehensive Organic Synthesis," ed by B. M. Trost and I. Fleming, Pergamon Press, Oxford (1991), Vol. 7, pp. 389-436; R. M. Hanson, Chem. Rev., 91, 437 (1991); A. Pfenniger, Synthesis, 1986, 89; B. E. Rossitier, "Asymmetric Synthesis," ed by J. D. Morrison, Academic Press, New York (1985), Vol. 5, pp. 193-246; C. H. Behrens and K. B. Sharpless, Aldrichimica Acta, 16, 67 (1983); A. S. Rao, S. K. Paknikar, and J. G. Kirtane, Tetrahedron, 39, 2323 (1983).
7. G. H. Posner, Org. React. (N. Y.), 22, 253 (1975); R. W. Herr, D. M. Wieland, and C. R. Johnson, J. Am. Chem. Soc., 92, 3813 (1970).
8. G. H. Posner, Org. React. (N. Y.), 22, 253 (1975); R. W. Herr, D. M. Wieland, and C. R. Johnson, J. Am. Chem. Soc., 92, 3813 (1970).
9. H. Z. Sable and J. G. Buchanan, "Selective Organic Transformations," ed by B. S. Thyagarajan, Wiley-Interscience, New York (1972), Vol. 2; B. C. Hartman and B. Rickborn, J. Org. Chem., 37, 4246 (1972); B. C. Hartman, T. Livinghouse, and B. Rickborn, J. Org. Chem., 38, 4346 (1973).
10. H. Z. Sable and J. G. Buchanan, "Selective Organic Transformations," ed by B. S. Thyagarajan, Wiley-Interscience, New York (1972), Vol. 2; B. C. Hartman and B. Rickborn, J. Org. Chem., 37, 4246 (1972); B. C. Hartman, T. Livinghouse, and B. Rickborn, J. Org. Chem., 38, 4346 (1973).
11. H. Z. Sable and J. G. Buchanan, "Selective Organic Transformations," ed by B. S. Thyagarajan, Wiley-Interscience, New York (1972), Vol. 2; B. C. Hartman and B. Rickborn, J. Org. Chem., 37, 4246 (1972); B. C. Hartman, T. Livinghouse, and B. Rickborn, J. Org. Chem., 38, 4346 (1973).
12. H. M. Fales and W. C. Wildman, J. Org. Chem., 26, 181 (1961).
13. a) L. A. Flippin, P. A. Brown, and K. Jalali-Araghi, J. Org. Chem., 54, 3588 (1989)
14. b) A. Pfaltz and A. Mattenberger, Angew. Chem., Suppl., 1982, 161.
15. a) M. Caron, P. R. Carlier, and K. B. Sharpless, J. Org. Chem., 53, 5185 (1988)
16. b) M. Onaka, K. Sugita, H. Takeuchi, and Y. Izumi, J. Chem. Soc., Chem. Commun., 1988, 1173
17. c) C. H. Behrens and K. B. Sharpless, J. Org. Chem., 50, 5697 (1985)
18. d) B. H. Lipshutz, R. S. Wilhelm, J. A. Kozlowxki, and D. Parker, J. Org. Chem., 49, 3928 (1984)
19. e) T. Suzuki, H. Saimoto, H. Tomioka, K. Oshima, and H. Nozaki, Tetrahedron Lett., 23, 3597 (1982)
20. f) P. Ma, V. S. Martin, S. Masamune, K. B. Sharpless, and S. M. Viti, J. Org. Chem., 47, 1380 (1982)
21. g) R. D. Wood and B. Ganem, Tetrahedron Lett., 23, 707 (1982)
22. h) S. Danishefsky, M-Y. Tsai, and T. Kirahara, J. Org. Chem., 42, 394 (1977).
23. J. M. Chong and K. B. Sharpless, J. Org. Chem., 50, 1560 (1985).
24. a) D. M. Gill, N. A. Pegg, and C. M. Rayner, Tetrahedron, 52, 3609 (1996)
25. b) H. Miyauchi and N. Ohashi, Bull. Chem. Soc. Jpn., 68, 3591 (1995)
26. c) H. Miyauchi, T. Nakamura, and N. Ohashi, Bull. Chem. Soc. Jpn., 68, 1731 (1995)
27. d) A. R. Derzhinskii, L. D. Konyushkin, and A. I. Lutsenko, Izv. Akad. Nauk SSSR, Ser. Khim., 11, 2652 (1984).
28. K. Kudo, K. Saigo, Y. Hahimoto, K. Saito, and M. Hasegawa, Chem. Lett., 1992, 1449; K. Kudo, Y. Hashimoto, H. Houchigai, M. Hasegawa, and K. Saigo, Bull. Chem. Soc. Jpn., 66, 848 (1993); K. Kudo, Y. Hashimoto, M. Sukegawa, M. Hasegawa, and K. Saigo, J. Org. Chem., 58, 579 (1993); Y. Hashimoto, Y. Sato, N. Takeshita, K. Kudo, and K. Saigo, Tetrahedron, 50, 8317 (1994); C. Liu, K. Kudo, Y. Hashimoto, and K. Saigo, J. Org. Chem., 61, 494 (1996).
29. K. Kudo, K. Saigo, Y. Hahimoto, K. Saito, and M. Hasegawa, Chem. Lett., 1992, 1449; K. Kudo, Y. Hashimoto, H. Houchigai, M. Hasegawa, and K. Saigo, Bull. Chem. Soc. Jpn., 66, 848 (1993); K. Kudo, Y. Hashimoto, M. Sukegawa, M. Hasegawa, and K. Saigo, J. Org. Chem., 58, 579 (1993); Y. Hashimoto, Y. Sato, N. Takeshita, K. Kudo, and K. Saigo, Tetrahedron, 50, 8317 (1994); C. Liu, K. Kudo, Y. Hashimoto, and K. Saigo, J. Org. Chem., 61, 494 (1996).
30. K. Kudo, K. Saigo, Y. Hahimoto, K. Saito, and M. Hasegawa, Chem. Lett., 1992, 1449; K. Kudo, Y. Hashimoto, H. Houchigai, M. Hasegawa, and K. Saigo, Bull. Chem. Soc. Jpn., 66, 848 (1993); K. Kudo, Y. Hashimoto, M. Sukegawa, M. Hasegawa, and K. Saigo, J. Org. Chem., 58, 579 (1993); Y. Hashimoto, Y. Sato, N. Takeshita, K. Kudo, and K. Saigo, Tetrahedron, 50, 8317 (1994); C. Liu, K. Kudo, Y. Hashimoto, and K. Saigo, J. Org. Chem., 61, 494 (1996).
31. K. Kudo, K. Saigo, Y. Hahimoto, K. Saito, and M. Hasegawa, Chem. Lett., 1992, 1449; K. Kudo, Y. Hashimoto, H. Houchigai, M. Hasegawa, and K. Saigo, Bull. Chem. Soc. Jpn., 66, 848 (1993); K. Kudo, Y. Hashimoto, M. Sukegawa, M. Hasegawa, and K. Saigo, J. Org. Chem., 58, 579 (1993); Y. Hashimoto, Y. Sato, N. Takeshita, K. Kudo, and K. Saigo, Tetrahedron, 50, 8317 (1994); C. Liu, K. Kudo, Y. Hashimoto, and K. Saigo, J. Org. Chem., 61, 494 (1996).
32. K. Kudo, K. Saigo, Y. Hahimoto, K. Saito, and M. Hasegawa, Chem. Lett., 1992, 1449; K. Kudo, Y. Hashimoto, H. Houchigai, M. Hasegawa, and K. Saigo, Bull. Chem. Soc. Jpn., 66, 848 (1993); K. Kudo, Y. Hashimoto, M. Sukegawa, M. Hasegawa, and K. Saigo, J. Org. Chem., 58, 579 (1993); Y. Hashimoto, Y. Sato, N. Takeshita, K. Kudo, and K. Saigo, Tetrahedron, 50, 8317 (1994); C. Liu, K. Kudo, Y. Hashimoto, and K. Saigo, J. Org. Chem., 61, 494 (1996).
33. I. Nakagawa, K. Aki, and T. Hata, J. Chem. Soc., Perkin Trans. 1, 1983, 1315.
34. J.-L. Namy and G. Boireau, Bull. Soc. Chem. Fr., 1971, 3191.
35. M. Chini, P. Crotti, A. A. Flippin, C. Cardelli, E. Giovani, F. Macchia, and M. Pineschi, J. Org. Chem., 58, 1221 (1993).
36. M. Shimagaki, T. Maeda, Y. Matsuzaki, I. Hiro, T. Nakata, and T. Oishi, Tetrahedron Lett., 25, 4775 (1984).
37. K. Mori, H. Kiyota, and D. Rochat, Liebigs Ann. Chem., 1993, 865.
38. K. Mori, H. Kiyota, C. Malosse, and D. Rochat, Liebigs Ann. Chem., 1993, 1201.
39. K. Mori, Tetrahedron, 33, 289 (1977); K. Mori and H. Iwasawa, Tetrahedron, 36, 2209 (1980).
40. K. Mori, Tetrahedron, 33, 289 (1977); K. Mori and H. Iwasawa, Tetrahedron, 36, 2209 (1980).
41. Y. Kitano, T. Matsumoto, and F. Sato, Tetrahedron, 44, 4073 (1988).
42. V. S. Martin, S. S. Woodard, T. Katsuki, Y. Yamada, M. Ikeda, and K. B. Sharpless, J. Am. Chem. Soc., 103, 6237 (1981).
43. K. A. M. Walker, Tetrahedron Lett., 18, 4475 (1977).
44. I. Paterson and I. Fleming, Tetrahedron Lett., 20, 995 (1979).
45. E. Negishi, T. Takahashi, and S. Baba, Org. Synth., 66, 60 (1987).
46. J. Fried, C. -H. Lin, and S. H. Ford, Tetrahedron Lett., 1969, 1379.
47. R. Mozingo, Org. Synth., Coll. Vol. III, 181 (1995).
48. a) A. Yasuda, S. Tanaka, H. Yamamoto, and H. Nozaki, Bull. Chem. Soc. Jpn., 52, 170 (1979)
49. b) T. Itoh, K. Jitsukawa, K. Kaneda, and S. Teranishi, J. Am. Chem. Soc., 101, 159 (1979).
50. X.-P. Gu, I. Ikeda, and M. Okahara, Bull. Chem. Soc. Jpn., 60, 667 (1987).
51. "CRYSTAN-GM, A Computar Program for the Solution and Refinement of Crystal Structures for X-Ray Diffraction Data," MAC Science Corporation.
52. M. Behforouz and J. E. Kerwood, J. Org. Chem., 34, 51 (1969).