Mercuracarborand-catalyzed Diels-Alder reactions of a thionoester with cyclopentadiene

Tetrahedron Letters

Volumn 40, Issue 43, 1999, Pages 7651-7655

  Hans, Lee ^a   Diaz, Martin ^a   Hawthorne, M Frederick ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Carboranes; Catalysis; Mercury; Thiocarbonyl compounds

Indexed keywords

CARBORANE DERIVATIVE; CYCLOPENTADIENE DERIVATIVE; ESTER DERIVATIVE; MERCURY;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL MODIFICATION; COMPLEX FORMATION;

BETULACEAE;

EID: 0033595859     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01582-8     Document Type: Article

References (40)

1. (a) Oh, T.; Reilly, M. Org. Prep. Proced. Int. 1994, 26, 129.
2. (b) Kagan, H. B.; Riant, O. Chem. Rev. 1992, 92, 1007.
3. (a) Asao, N.; Kii, S.; Hanawa, H.; Maruoka, K. Tetrahedron Lett. 1998, 39, 3729.
4. (b) Ooi, T.; Takahashi, M.; Maruoka, K. J. Am. Chem. Soc. 1996, 118, 11307.
5. (c) Adams, R. D.; Chen, G.; Chen, L.; Wu, W.; Yin, J. J. Am. Chem. Soc. 1991, 113, 9406.
6. (a) Vaugeois, J.; Simard, M.; Wuest, J. D. Organometallics 1998, 17, 1215.
7. (b) Simard, M.; Vaugeois, J.; Wuest, J. D. J. Am. Chem. Soc. 1993, 115, 370.
8. (c) Sharma, V.; Simard, M.; Wuest, J. D. J. Am. Chem. Soc. 1992, 114, 7931.
9. Vaugeois, J.; Simard, M.; Wuest, J. D. Coord. Chem. Rev. 1995, 145, 55.
10. Wuest, J. D.; Zacharie, B. J. Am. Chem. Soc. 1985, 107, 6121.
11. (a) Kohler, J. U.; Lewis, J.; Raithby, P. R. Angew. Chem. Int. Ed. Engl. 1996, 35, 993.
12. (b) Alper, H.; Silavwe, N. D.; Birnbaum, G. I.; Ahmed, F. R. J. Am. Chem. Soc. 1979, 101, 6582.
13. (a) Saito, T.; Fujii, H.; Hayashibe, S.; Matsushita, T.; Kato, H.; Kobayashi, K. J. Chem. Soc., Perkin Trans. 1 1996, 1897.
14. (b) Braddock, D. C.; Brown, J. M.; Guiry, P. J. J. Chem. Soc., Chem. Commun. 1993, 1244.
15. (c) Motoki, S.; Saito, T.; Karakasa, T.; Kato, H.; Matsushita, T.; Hayashibe, S. J. Chem. Soc., Perkin Trans. 1 1991, 2281.
16. (a) Yang, X.; Zheng, Z.; Knobler, C. B.; Hawthorne, M. F. J. Am. Chem. Soc. 1993, 115, 193.
17. (b) Yang, X.; Knobler, C.B.; Hawthorne, M. F. Angew. Chem., Int. Ed. Engl. 1991, 30, 1507.
18. (a) Hawthorne, M. F.; Zheng, Z. Acc. Chem. Res. 1997, 30, 267.
19. (b) Zheng, Z.; Knobler, C. B.; Hawthorne, M. F. J. Am. Chem. Soc. 1995, 117, 5105.
20. (c) Yang, X.; Zheng, Z.; Knobler, C. B.; Hawthorne, M. F. J. Am. Chem. Soc. 1994, 116, 7142.
21. (d) Hawthorne, M. F.; Yang, X.; Zheng, Z. Pure Appl. Chem. 1994, 66, 245.
22. (e) Yang, X.; Knobler, C. B.; Hawthorne, M. F. J. Am. Chem. Soc. 1992, 114, 380.
23. For references to recent work on multidentate Lewis acids, see: (a) Vaugeois, J.; Wuest, J. D. J. Am. Chem. Soc. 1998, 720, 13016.
24. (b) Tschinkl, M.; Schier, A.; Riede, J.; Gabbai, F. P. Inorg. Chem. 1997, 36, 5706.
25. (c) Saied, O.; Simard, M.; Wuest, J. D. Organometallics 1996, 2345.
26. (d) Reilly, M.; Oh, T. Tetrahedron Lett. 1995, 36, 217.
27. (a) Zinn, A. A.; Zheng, Z.; Knobler, C. B.; Hawthorne, M. F. J. Am. Chem. Soc. 1996, 118, 70.
28. (b) Zheng, Z.; Knobler, C. B.; Mortimer, M. D.; Kong, G.; Hawthorne, M. F. Inorg. Chem. 1996, 35, 1235.
29. (a) Synthesized using trimethyloxonium tetrafluoroborate using the method of: Hoffman, R.; Hartke, K. Chem. Ber. 1980, 113, 919.
30. (b) Alternatively from O-methyl (dimethoxyphoshinyl)-thioacetate using the method of: Hartke, K.; Kunze, O.; Hoederath, W. Synthesis 1985, 960.
31. 4 instead of AgOAc was used to form empty host 1.
32. +).
33. +).
34. Zakharkin, L. I.; Bregadze, V. I.; Okhlobystin, O. Y. J. Organometal. Chem. 1965, 4, 211.
35. 11B NMR spectra is identical to that of 1-3, respectively.
36. Maciel, G. E.; Borzo, M. J. Magn. Reson. 1973, 10, 388.
37. 2. Sens, M. A.; Wilson, N. K.; Ellis, P. D.; Odom, J. D. J. Magn. Reson. 1975, 19, 323.
38. 1H} NMR spectra were recorded at 25°C with a Bruker 500 spectrometer at 89.6 MHz by using broad-band decoupling.
39. Hammond, G. S. J. Am. Chem. Soc. 1955, 77, 334.
40. Lee, H.; Knobler, C. B.; Hawthorne, M. F. Unpublished results.