Construction of 1,3-oxathiane ring through Pummerer reaction of γδ- unsaturated sulfinyl compounds

Chemical and Pharmaceutical Bulletin

Volumn 45, Issue 5, 1997, Pages 778-785

  Abe, Hitoshi ^a   Fujii, Hiroyuki ^a   Masunari, Chieko ^a   Itani, Junko ^a   Kashino, Setsuo ^a   Shibaike, Kentaro ^a   Harayama, Takashi ^a  

^a OKAYAMA UNIVERSITY   (Japan)

Author keywords

Oxathiane; P toluenesulfonic acid; Pummerer rearrangement; Sulfinyl compound

Indexed keywords

SULFINYL DERIVATIVE; SULFUR DERIVATIVE; TOLUENESULFONIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CONFORMATION; REACTION ANALYSIS; SYNTHESIS;

EID: 0030918260     PISSN: 00092363     EISSN: None     Source Type: Journal    
DOI: 10.1248/cpb.45.778     Document Type: Article

References (63)

1. a) Fuji K., Ueda M., Fujita E., J. Chem. Soc., Chem. Commun., 1977, 814;
2. b) Fuji K., Ueda M., Sumi K., Fujita E., Tetrahedron Lett., 22, 2005-2008 (1981);
3. c) Fuji K., Ueda M., Fujita E., J. Chem. Soc., Chem. Commun., 1983, 49-50;
4. d) Fuji K., Ueda M., Sumi K., Kajiwara K., Fujita E., Iwashita T., Miura I., J. Org. Chem., 50, 657-661 (1985);
5. e) Fuji K., Ueda M., Sumi K., Fujita E., J. Org. Chem., 50, 662-666 (1985).
6. a) Ogura K., Tsuchihashi G., Tetrahedron Lett., 1971, 3151-3154;
7. b) Idem, ibid., 1972, 1383-1386;
8. c) Idem, J. Am. Chem. Soc., 96, 1960-1962 (1974);
9. d) Ogura K., Yamashita M., Suzuki M., Tsuchihashi G., Tetrahedron Lett., 1974, 3653-3656;
10. e) Ogura K., Yoshimura I., Katoh N., Tsuchihashi G., Chem. Lett., 1975, 903-804;
11. f) Ogura K., Yamashita M., Furukawa S., Suzuki M., Tsuchihashi G., Tetrahedron Lett., 1975, 2767-2770;
12. g) Ogura K., Yamashita M., Tsuchihashi G., ibid., 1976, 759-762;
13. h) Ogura K., Katoh N., Yoshimura I., Tsuchihashi G., ibid., 1978, 375-378;
14. i) Ogura K., Itoh Y., Tsuchihashi G., Bull. Chem. Soc. Jpn., 52, 2013-2022 (1979);
15. j) Ogura K., Yamashita M., Suzuki M., Furukawa S., Tsuchihashi G., ibid., 57, 1637-1642 (1984).
16. a) Ogura K., Yahata N., Watanabe J., Takahashi K., Iida H., Bull. Chem. Soc. Jpn., 56, 3543-3544 (1983);
17. b) Ogura K., Yahata N., Hashizume K., Tsuyama K., Takahashi K., Iida H., Chem. Lett., 1983, 767-770;
18. c) Ogura K., Ohtsuki K., Nakamura M., Yahata N., Takahashi K., Iida H., Tetrahedron Lett., 26, 2455-2458 (1985).
19. Seebach D., Synthesis, 1969, 17-36.
20. a) Eliel E. L., Koskimies J. K., Lohri B., J. Am. Chem. Soc., 100, 1614-1616 (1978);
21. b) Eliel E. L., Frazee W. J., J. Org. Chem., 44, 3598-3599 (1979);
22. c) Eliel E. L., Lynch J. E., Tetrahedron Lett., 22, 2855-2858 (1981);
23. d) Eliel E. L., Soai K., ibid., 22, 2859-2862 (1981);
24. e) Eliel E. L., Morris-Natschke S., J. Am. Chem. Soc., 106, 2937-2942 (1984);
25. f) Lynch J. E., Eliel E. L., ibid., 106, 2943-2948 (1984);
26. g) Ko K.-Y., Frazee W. J., Eliel E. L., Tetrahedron, 40, 1333-1343 (1984);
27. h) Frye S. V., Eliel E. L., Tetrahedron Lett., 26, 3907-3910 (1985);
28. i) Ko K.-Y., Eliel E. L., J. Org. Chem., 51, 5353-5362 (1986);
29. j) Frye S. V., Eliel E. L., J. Am. Chem. Soc., 110, 484-489 (1988);
30. k) Isobe M., Obeyama J., Funabashi Y., Goto T., Tetrahedron Lett., 29, 4773-4776 (1988);
31. l) Utimoto K., Nakamura A., Matsubara S., J. Am. Chem. Soc., 112, 8189-8190 (1990).
32. a) Pihlaja K., Pasanen P., Acta Chem. Scand., 24, 2257-2258 (1970);
33. b) Pasanen P., Pihlaja K., ibid., 25, 1908-1910 (1971);
34. c) Danneels D., Anteunis M., van Acker L., Tavernier D., Tetrahedron, 31, 327-331 (1975);
35. d) Greene T. W., "Protective Groups in Organic Synthesis," John Wiley & Sons, New York, 1981, pp. 138-140.
36. a) Oae S., Numata T., Tetrahedron, 30, 2641-2646 (1974);
37. b) Numata T., Oae S., ibid., 32, 2699-2703 (1976);
38. c) Findlay J. B. C., Fishwick C. W. G., Kersey I. D., Ward P., Tetrahedron Lett., 36, 2299-2302 (1995);
39. d) Kersey I. D., Fishwick C. W. G., Findlay J. B. C., Ward P., Tetrahedron, 51, 6819-6834 (1995).
40. De Lucchi O., Miotti U., Modena G., Org. React., 40, 157-405 (1991).
41. A part of this work has been published in a preliminary communication: Abe H., Itani J., Masunari C., Kashino S., Harayama T., J. Chem. Soc., Chem. Commun., 1995, 1197-1198.
42. a) Paquette L. A., Moerck R.E., Harirchian B., Magnus P. D., J. Am. Chem. Soc., 100, 1597-1599 (1978);
43. b) Danishefsky S., Harayama T., Singh R. K., ibid., 101, 7008-7012 (1979);
44. c) Maignan C., Raphael R., Tetrahedron, 39, 3245-3249 (1983).
45. 10c) could be deduced from theoretical studies on the stereochemical features of vinyl sulfoxide; a) Kahn S. D., Hehre W. J., J. Am. Chem. Soc., 108, 7399-7400 (1986); b) Idem, Tetrahedron Lett., 27, 6041-6044 (1986).
46. 10c) could be deduced from theoretical studies on the stereochemical features of vinyl sulfoxide; a) Kahn S. D., Hehre W. J., J. Am. Chem. Soc., 108, 7399-7400 (1986); b) Idem, Tetrahedron Lett., 27, 6041-6044 (1986).
47. a) Jung M. E., Grove D. D., J. Chem. Soc., Chem. Commun., 1987, 753-755;
48. b) Ono N., Kamimura A., Kaji A., J. Org. Chem., 53, 251-258 (1988).
49. a) Fuji K., Tanaka K., Abe H., Itoh A., Node M., Taga T., Miwa Y., Shiro M., Tetrahedron: Asymmetry, 2, 179-182, 1319-1327 (1991);
50. b) Fuji K., Tanaka K., Abe H., Matsumoto K., Taga T., Miwa Y., ibid., 3, 609-612 (1992);
51. c) Fuji K., Tanaka K., Abe H., Matsumoto K., Harayama T., Ikeda A., Taga T., Miwa Y., Node M., J. Org. Chem., 59, 2211-2218 (1994).
52. Johnson C. K., ORTEP II, Report ORNL-5138, Oak Ridge National Laboratory, Tennessee, U.S.A., 1976.
53. Corey E. J., Erickson B. W., J. Org. Chem., 36, 3553-3560 (1971).
54. Although no minor oxathiane was detected in the reaction with 4, the relative configuration of 28 was elucidated as depicted in Table 2, based upon studies on the conformational features of 1,3-oxathiane derivatives. Since it has been documented that 2-alkylated-1,3-oxathianes generally exist in a chair conformation, the 2-alkyl group should be in equatorial direction, in order to avoid steric interaction. a) Gelan J., Anteunis M., Bull. Soc. Chim. Belges, 77, 423-432 (1968); b) Idem, ibid., 77, 447-454 (1968); c) Pasanen P., Pihlaja K., Tetrahedron, 28, 2617-2626 (1972).
55. Although no minor oxathiane was detected in the reaction with 4, the relative configuration of 28 was elucidated as depicted in Table 2, based upon studies on the conformational features of 1,3-oxathiane derivatives. Since it has been documented that 2-alkylated-1,3-oxathianes generally exist in a chair conformation, the 2-alkyl group should be in equatorial direction, in order to avoid steric interaction. a) Gelan J., Anteunis M., Bull. Soc. Chim. Belges, 77, 423-432 (1968); b) Idem, ibid., 77, 447-454 (1968); c) Pasanen P., Pihlaja K., Tetrahedron, 28, 2617-2626 (1972).
56. Although no minor oxathiane was detected in the reaction with 4, the relative configuration of 28 was elucidated as depicted in Table 2, based upon studies on the conformational features of 1,3-oxathiane derivatives. Since it has been documented that 2-alkylated-1,3-oxathianes generally exist in a chair conformation, the 2-alkyl group should be in equatorial direction, in order to avoid steric interaction. a) Gelan J., Anteunis M., Bull. Soc. Chim. Belges, 77, 423-432 (1968); b) Idem, ibid., 77, 447-454 (1968); c) Pasanen P., Pihlaja K., Tetrahedron, 28, 2617-2626 (1972).
57. Ruff F., Kucsman A., J. Chem. Soc., Perkin Trans. 2, 1988, 1123-1128.
58. a) Böhme H., Bentler H., Chem. Ber., 89, 1464-1468 (1956);
59. b) Okuyama T., Nakada M., Fueno T., Tetrahedron, 32, 2249-2252 (1976).
60. Node M., Itoh A., Nishide K., Abe H., Kawabata T., Masaki Y., Fuji K., Synthesis, 1992, 1119-1124.
61. Gilmore C. J., J. Appl. Cryst., 17, 42-46 (1984).
62. Cromer D. T., Weber J. T., "International Tables for X-Ray Crystallography," Vol. 4, The Kynoch Press, Birmingham, 1974, Table 2.2 A.
63. TEXSAN-TEXRAY Structure Analysis Package, Molecular Structure Corporation, 3200 Research Forest Drive, The Woodlands, Texas 77381, U.S.A.