Intramolecular Diels-Alder reactions of 2H-thiopyran dienes

Canadian Journal of Chemistry

Volumn 74, Issue 7, 1996, Pages 1418-1436

  Ward, Dale E ^a   Nixey, Thomas E ^a   Gai, Yuanzhu ^a   Hrapchak, Matthew J ^a   Abaee, M Saeed ^a  

^a UNIVERSITY OF SASKATCHEWAN   (Canada)

Author keywords

2H thiopyran; cis substituted 1,3 diene surrogate; Intramolecular Diels Alder; trans decahydro 4a methylnapthalene derivatives; trans octahydro 3a methyl 1H indene derivatives

Indexed keywords

CATALYSIS; CATALYST SELECTIVITY; DERIVATIVES; DESULFURIZATION; HYDROCARBONS; ISOMERIZATION; MIXTURES; OLEFINS;

INTRAMOLECULAR DIELS-ALDER REACTION; LEWIS ACID CATALYSIS; STEREOSELECTIVITY;

CHEMICAL REACTIONS;

EID: 0030190664     PISSN: 00084042     EISSN: None     Source Type: Journal    
DOI: 10.1139/v96-160     Document Type: Article

References (91)

1. O. Diels and K. Alder. Justus Liebigs Ann. Chem. 460, 98 (1928).
2. (a) F. Fringuelli and A. Taticchi. In Dienes in the Diels-Alder reaction. Wiley, New York. 1990;
3. (b) W. Carruthers. In Cycloaddition reactions in organic synthesis. Pergamon, Oxford. 1990;
4. (c) G. Desimoni, G. Tacconi, A. Barcoa, and G.P. Pollini. In Natural product synthesis through pericyclic reactions. ACS Monograph 180. American Chemical Society, Washington. 1983;
5. (d) B.M. Trost and I. Flemming (Editors). Comprehensive organic synthesis. Vol. 5. Pergamon Press, Oxford. 1991. Chap. 4.
6. (a) J.G. Martin and R.K. Hill. Chem. Rev. 61, 537 (1961);
7. (b) J. Sauer. Angew. Chem. Int. Ed. Engl. 6, 16 (1967).
8. D.E. Ward, W.M. Zoghaib, C.K. Rhee, and Y. Gai. Tetrahedron Lett. 31, 845 (1990).
9. D.E. Ward, Y. Gai, and W.M. Zoghaib. Can. J. Chem. 69, 1487 (1991).
10. D.E. Ward and Y. Gai. Tetrahedron Lett. 33, 1851 (1992).
11. D.E. Ward and Y. Gai. Can. J. Chem. 70, 2627 (1992).
12. D.E. Ward and TE. Nixey. Tetrahedron Lett. 34, 947 (1993).
13. D.E. Ward, Y. Gai, and Y. Lai. Synlett, 261 (1996).
14. (a) W.R. Roush. In Comprehensive organic synthesis. Vol. 5. Edited by B.M. Trost and I. Flemming. Pergamon, Oxford. 1991. Chap. 4.4;
15. (b) W.R. Roush. In Advances in cycloaddition. Vol. 2. Edited by D.P. Curran. JAI Press, Greenwich, Conn. 1990. p. 91;
16. (c) M.J. Taschner. In Organic synthesis: theory and application. Vol. 1. Edited by T. Hudlicky. JAI Press, Greenwich, Conn. 1989. p. 79;
17. (d) D. Craig. Chem. Soc. Rev. 16, 187 (1987);
18. (e) A. Fallis. Can. J. Chem. 62, 183 (1984);
19. (f) E. Ciganek. Org. React. 32, 1 (1984);
20. (g) D.F. Taber. In Intramolecular Diels-Alder and ene reactions. Springer-Verlag, Berlin. 1984;
21. (h) L.A. Paquette. In Asymmetric synthesis. Vol. 3. Edited by J.D. Morrison. Academic Press, New York. 1984. Chap. 7;
22. (i) G. Brieger and J.N. Bennett. Chem. Rev. 80, 63 (1980);
23. (j) R. Funk, and K.P.C. Vollhardt. Chem. Soc. Rev. 9, 41 (1980);
24. (k) W. Oppolzer. Synthesis, 793 (1978);
25. (l) Angew. Chem. Int. Ed. Engl. 16, 10 (1977);
26. (m) G. Mehta. J. Chem. Educ. 53, 551 (1976);
27. (n) R.G. Carlson. Annu. Rep. Med. Chem. 9, 270 (1974).
28. W.R. Roush, A.I. Ko, and H.R. Gillis. J. Org. Chem. 45, 4264 (1980).
29. (a) K.R. Buszek. Tetrahedron Lett. 36, 9125 (1995);
30. (b) P.A. Wender and T.E. Smith. J. Org. Chem. 60, 2962 (1994);
31. (c) S.F. Martin, Y. Liao, Y. Wong, and T. Rein. Tetrahedron Lett. 35, 691 (1995);
32. (d) M. Sodeoka, H. Yamada, and M. Shibasaki. J. Am. Chem. Soc. 112, 4906 (1990);
33. (e) S.-S.P. Chou and S.-J. Wey. J. Org. Chem. 55, 1270 (1990);
34. (f) S. Wattanasin, F.G. Kathawala, and R.K. Boeckman. J. Org. Chem. 50, 3810 (1985);
35. (g) M. Yoshida, H. Nakai, and M. Ohno. J. Am. Chem. Soc. 106, 1133 (1984);
36. (h) M. Koreeda and J.I. Luengo. J. Org. Chem. 49, 2079 (1984);
37. (i) S.F. Martin, S.A. Williamson, R.P. Gist, and K.M. Smith. J. Org. Chem. 48, 5170 (1983);
38. (j) R.K. Boeckman, and T.R. Alessi. J. Am. Chem. Soc. 104, 3216 (1982);
39. (k) S.G. Pyne, M.J. Hensel, and P.J. Fuchs. J. Am. Chem. Soc. 104, 5719 (1982);
40. (l) M.E. Kuehne, T.H. Matsko, J.C. Bohnert, L. Motyka, and D. Oliver-Smith. J. Org. Chem. 46, 2002 (1981);
41. (m) W. Oppolzer, C. Fehr, and J. Warneke. Helv. Chim. Acta, 60, 48 (1977);
42. (n) R.F. Borch, A.J. Evans, and J.J. Wade. J. Am. Chem. Soc. 99, 1612 (1977);
43. (o) H.O. House and T.H. Cronin. J. Org. Chem. 30, 1061 (1965).
44. (a) T.K. Park, I.J. Kim, S.J. Danishefsky, and S. de Gala. Tetrahedron Lett. 36, 1019 (1995);
45. (b) J.D. Winkler, H.S. Kim, and S. Kim. Tetrahedron Lett. 36, 687 (1995);
46. (c) M.Y. Chu-Moyer, S.J. Danishefsky, and G.K. Schulte. J. Am. Chem. Soc. 116, 11213 (1994);
47. (d) R.W. Jackson and K.J. Shea. Tetrahedron Lett. 35, 1317 (1994);
48. (e) I. Hanna, J.-Y. Lallemand, and P. Wlodyka. Tetrahedron Lett. 35, 6685 (1994);
49. (f) A. Tahri, D. Uguen, A. De Cain, and J. Fischer. Tetrahedron Lett. 35, 3945 (1994);
50. (g) R.V. Bonnert and P.R. Jenkins. J. Chem. Soc. Perkin Trans. 1, 413 (1989);
51. (h) K.J. Shea and C.D. Haffner. Tetrahedron Lett. 29, 1367 (1988);
52. (i) E.J. Corey, P.D.S. Jardine, and J.C. Rohloff. J. Am. Chem. Soc. 110, 3672 (1988);
53. (j) J.-F. He and Y.-L. Wu. Tetrahedron, 44, 1933 (1988);
54. (k) F.E. Ziegler, B.H. Jaynes, and M.T. Saindane. J. Am. Chem. Soc. 109, 8115 (1987);
55. (l) P. Magnus, C. Walker, P.R. Jenkins, and K.A. Meanar. Tetrahedron Lett. 27, 651 (1986);
56. (m) K.C. Nicolaou and W.S. Li. J. Chem. Soc. Chem. Commun. 421 (1985);
57. (n) P.R. Jenkins, K.A. Menear, P. Barraclough, and M.S. Nobbs. J. Chem. Soc. Chem. Commun. 1423 (1984);
58. (o) K.J. Shea and P.D. Davis. Angew. Chem. Int. Ed. Engl. 22, 419 (1983).
59. T. Saito, T. Shizuta, H. Kikuchi, J. Nakagawa, K. Hirotsu, H. Ohmura, and S. Motoki. Synthesis, 727 (1994).
60. (a) E.A. Fehnel and M. Carmack. J. Am. Chem. Soc. 70, 1813 (1948);
61. (b) N.G. Rule, M.R. Detty, J.E. Kaeding, and J.A. Sinicropi. J. Org. Chem. 60, 1665 (1995);
62. (c) S. Tamai, H. Ushirogochi, S. Sano, and Y. Nagao. Chem. Lett. 295 (1995).
63. (a) T. Takemura and J.B. Jones. J. Org. Chem. 48, 791 (1983);
64. (b) S. Lane, S.J. Quick, and R.J.K. Taylor. J. Chem. Soc. Perkin Trans. 1, 893 (1985);
65. (c) H. Matsuyama, Y. Takei, and M. Kobayashi. Bull. Chem. Soc. Jpn. 59, 2657 (1986);
66. (d) H. Matsuyama, Y. Miyazawa, Y. Takei, and M. Kobayashi. J. Org. Chem. 52, 1703 (1987);
67. (e) T. Fujisawa, B.I. Mobele, and M. Shimizu. Tetrahedron Lett. 32, 7055 (1991).
68. G.A. Krause and K. Landgrebe. Synthesis, 885 (1984).
69. R.J. Batten, J.D. Coyle, R.J.K. Taylor, and S. Vassiliou. J. Chem. Soc. Perkin Trans, 1, 1177 (1982).
70. C.H. Chen, G.A. Reynolds, and J.H. Van Allan. J. Org. Chem. 42, 2777 (1977).
71. V.K. Kansal and R.J.K. Taylor. J. Chem. Soc. Perkin Trans. 1, 703 (1984).
72. S. Lane, S.J. Quick, and R.J.K. Taylor. J. Chem. Soc. Perkin Trans. 1, 2549 (1984).
73. G. Casy, A.G. Sutherland, R.J.K. Taylor, and P.G. Urben. Synthesis, 767 (1989).
74. E. Vedejs, M.J. Arnost, and J.P. Hagen. J. Org. Chem. 44, 3230 (1979).
75. (a) S.U. Kulkarni and V.D. Patil. Heterocycles 18, 163 (1982);
76. (b) J.K. Baker and T.L. Little. J. Med. Chem. 28, 46 (1985).
77. H.O. House, V.K. Jones, and G.A. Frank. J. Org. Chem. 29, 3327 (1964).
78. (a) H. Lamy-Schelkens and L. Ghosez. Tetrahedron Lett. 30, 5891 (1989);
79. (b) H. Lamy-Schelkens, D. Giomi, and L. Ghosez. Tetrahedron Lett. 30, 5887 (1989).
80. K.J. Shea, S. Wise, L.D. Burke, P.D. Davis, J.W. Gilman, and A.C. Greeley, J. Am. Chem. Soc. 104, 5708 (1982).
81. D.T. Witiak, K. Tomita, and R.J. Patch. J. Med. Chem. 24, 788 (1981).
82. M. Bols and T. Skrydstrup. Chem. Rev. 95, 1253 (1995).
83. (a) M.E. Jung. Synlett, 186 (1990);
84. (b) M.E. Jung and J. Gervay. J. Am. Chem. Soc. 113, 224 (1991).
85. R.D. Little, M.R. Masjedizadeh, O. Wallquist, and J.I. McLaughlin. Org. React. 47, 315 (1995).
86. (a) W.R. Roush, H.R. Gillis, and A.I. Ko. J. Am. Chem. Soc. 104, 2269 (1982);
87. (b) W.R. Roush and H.R. Gillis. J. Org. Chem. 47, 4825 (1982).
88. W.C. Still, M. Kahn, and A. Mitra. J. Org. Chem. 43, 2923 (1978).
89. D.F. Taber. J. Org. Chem. 47, 1351 (1982).
90. D.W. Brown, T.T. Nakashima, and D.L. Rabenstein. J. Magn. Reson. 45, 302 (1981).
91. K.A. Walker, M.R. Boots, J.F. Stubbins, M.E. Rogers, and C.W. Davis. J. Med. Chem. 26, 174 (1983).