Direct synthesis of 2-norbornanone dithioacetals from 2-cyclopentenone dithioacetals and dienophiles. Synthetic application of thermal interconversion between cyclic dithioacetals and the ring-opened vinyl sulfide forms

Tetrahedron

Volumn 52, Issue 30, 1996, Pages 9979-9990

  Ohkita, Masakazu ^a   Nishizawa, Osamu ^a   Imai, Toshiro ^a   Nishida, Shinya ^a   Tsuji, Takashi ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

NORBORNANE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; PRIORITY JOURNAL; REACTION ANALYSIS; TECHNIQUE;

EID: 0030598003     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00534-0     Document Type: Article

References (30)

1. 1. (a) Ohkita, M.; Tsuji, T.; Nishida, S. J. Chem. Soc., Chem. Commun. 1991, 37.
2. (b) Ohkita, M.; Nishizawa, O.; Tsuji, T.; Nishida, S. J. Org. Chem. 1993, 58, 5200.
3. 60): (a) Ohkita, M.; Ishigami, K.; Tsuji, T. J. Chem. Soc., Chem. Commun. 1995, 1769.
4. (b) Takeshita, H.; Liu, J.-F.; Kato, N.; Mori, A.; Isobe, R. Chem. Lett. 1995, 377.
5. 3. For acetalization of unsaturated carbonyls, see: (a) Meskens, F. A. J. Synthesis 1981, 501.
6. (b) Otera, J.; Dan-oh, N.; Nozaki, H. Tetrahedron 1992, 48, 1449.
7. (c) Tsunoda, T.; Suzuki, M.; Noyori, R. Tetrahedron Lett. 1980, 21, 1357.
8. (d) Dauben, W. G.; Gerdes, J. M.; Look, G. C. J. Org. Chem. 1986, 57, 4964.
9. (e) Hwu, J. R.; Wetzel, J. M. J. Org. Chem. 1985, 50, 3946.
10. (f) Hwe, J. R.; Leu, L.-C.; Robl, J. A.; Anderson, D. A.; Wetzel, J. M. J. Org. Chem. 1987, 52, 188.
11. 4. Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, Wiley, New York, 1991, p. 198.
12. 5. For a preliminary account of this work, see: Ohkita, M.; Nishizawa, O.; Tsuji, T.; Nishida, S. J. Chem. Soc., Chem. Commun. 1993, 1676.
13. 6. Luh, T.-Y. Acc. Chem. Res. 1991, 24, 257.
14. 7. Rosini, G.; Spineti, G. G.; Foresti, E.; Pradella, G. J. Org. Chem. 1981, 46, 2228.
15. 8. Jackman, L. M.; Sternhell, S. Applications of Nuclear Magnetic Resonance Spectroscopy in Organic Chemistry, 2nd ed, Pergamon Press, Oxford, England, 1969.
16. 9. When the reaction was carried out using less than 1 equiv of dienophiles the formation of the isomeric adducts (up to 10% yield) was observed which was, however, completely prevented by using excess dienophiles (3 equiv) for the reaction.
17. 10. For the Diels-Alder reaction of hetero-substituted dienes, see: (a) Petrzilka, M.; Grayson, J. I. Synthesis 1981, 753.
18. (b) Fringuelli, F.; Taticchi, A. Dienes in The Diels-Alder Reaction; John Wiley & Sons: New York, 1990.
19. 3CN, 25 °C): δ 1.51 (s, 3 H), 1.62 (br. d, J = 8.8 Hz, 1 H), 1.66 (dd, J = 8.8, 2.0 Hz, 1 H), 2.65-3.02 (m, 4 H), 3.39 (d, J = 8.3 Hz, 1 H), 3.77 (dd, J = 8.3, 4.9 Hz, 1 H), 5.64 (s, 1 H).
20. 12. Ranganathan, S.; Ranganathan, D.; Mehrotra, A. K. Synthesis 1977, 289.
21. 13. Evans, D. A.; Scott, W. L.; Truesdale, L. K. Tetrahedron Lett. 1972, 13, 121.
22. 14. Irreversible cleavage of one of carbon-sulfur bonds in acyclic dithioacetals, see; (a) Rodriguez, A. D.; Nickon, A. Tetrahedron, 1985 41, 4443.
23. (b) Denis, J. N.; Krief, A. Tetrahedron Lett., 1982 23, 3407.
24. (c) Bartels, B.; Hunter, R.; Simon, C. D.; Tomlinson, G. D. Tetrahedron Lett. 1987, 28, 2985.
25. (d) Trost, B. M.; Lavoie, A. C. J. Am. Chem. Soc. 1983, 105, 5075.
26. (e) Cohen, T.; Herman, G.; Falck, J. R.; Mura, A. J., Jr. J. Org. Chem. 1975, 40, 812.
27. 15. Shih, C.; Swenton, J. S. J. Org. Chem. 1982, 47, 2825.
28. 16. Suzuki, M.; Oda, Y.; Noyori, R. J. Am. Chem. Soc. 1979, 101, 1623.
29. 17. Cooke, F.; Moerck, R.; Schwindeman, J.; Magnus, P. J. Org. Chem. 1980, 45, 1046.
30. 18. Miyashita, M.; Yanami, T.; Yoshikoshi, A. J. Am. Chem. Soc. 1976, 98, 4679.