Aluminum chloride catalyzed stereoselective [3 + 2] cycloaddition of allylsilanes with simple conjugated dienes

Organometallics

Volumn 16, Issue 24, 1997, Pages 5158-5162

  Choi, Geun Mook ^b   Yeon, Seoung Ho ^a   Jin, Jungil ^b   Yoo, Bok Ryul ^a   Jung, Il Nam ^a  

^a Korea Institute of Science and Technology   (South Korea)

^b Korea University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000446955     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om970603s     Document Type: Article

References (34)

1. (a) Ramaiah, M. Synthesis 1984, 529.
2. (b) Hudlicky, T.; Rulin, F.; Lovelace, T. C.; Reed J. W. In Studies in Natural Products Chemistry; Attauer-Raman, T., Ed.; Elsevier Science: Sussex, U.K, 1989; p 3.
3. (c) Ho, T.-L. Carbocyclic Constructions in Terpene Synthesis; VCH: New York, 1988.
4. Knölker, H.-J.; Jones, P. G.; Pannek, J.-B. Synlett 1990, 429.
5. Knölker, H.-J.; Jones, P. G.; Pannek, J.-B.; Weinkauf, A. Synlett 1991, 147.
6. Danheiser, R.-L.; Dixon, B.-R.; Gleason, R.-W. J. Org. Chem. 1992, 57, 6094.
7. Yamaguchi, M.; Sehata, M.; Hayashi, A.; Hirama, M. J. Chem. Soc., Chem. Commun. 1993, 1708.
8. (a)Knölker, H.-J.; Graf, R. ; Pannek, J.-B. Tetrahedron 1993, 49, 9955.
9. (b) Knölker, H.-J.; Foitzik, N.; Goesmann, H.; Graf, R.; Jones, P.; Wanzl, G. Chem. Eur. J. 1997, 3, 538.
10. Knölker, H.-J.; Foitzik, N.; Goesmann, H.; Graf, R. Angew. Chem., Int. Ed. Engl. 1993, 32, 1081.
11. (a) Knölker, H.-J.; Graf, R. Tetrahedron Lett. 1993, 34, 4765.
12. (b) Knölker, H.-J.; Jones, P. G.; Pannek, J.-B. Synlett 1994, 131.
13. Akiyama, T.; Ishikawa, K.; Ozaki, S. Chem. Lett. 1994, 627.
14. Akiyama, T.; Yasusa, T.; Ishikawa, K.; Ozaki, S. Tetrahedron Lett. 1994, 35, 8401.
15. Stahl, A.; Steckhan, E.; Nieger, M. Tetrahedron Lett. 1994, 35, 7371.
16. Kiyooka, S.; Shiomi, Y.; Kira, H; Kaneko, Y.; Tanimora, S. J. Org. Chem. 1994, 59, 1958.
17. Knölker, H.-J. J. Prakt. Chem. 1997, 304.
18. Yeon, S. H.; Lee, B. W.; Yoo, B. R.; Suk, M. Y.; Jung, I. N. Organometallics 1995, 14, 2361.
19. Yeon, S. H.; Han, J. S.; Hong, E.; Do, Y.; Jung, I. N. J. Organomet. Chem. 1995, 499, 159.
20. Cho, B. K.; Choi, G. M.; Jin, J.-I.; Yoo, B. R.; Jung, I. N. Organometallics 1997, 16, 3576.
21. (a) Asao, N.; Yoshikawa, E.; Yamamoto, Y. J. Org. Chem. 1996, 61, 4874.
22. (b) Yoshikawa, E.; Gevorgyan, V.; Asao, N.; Yamamoto, Y. J. Am. Chem. Soc. 1997, 119, 6781.
23. Kamigaito, M.; Sawamoto, M.; Hiagshimura, T. J. Polym. Sci., Part A: Polym. Chem. 1991, 29, 1909.
24. Peng, Y. X.; Shi, W. M. Polym. Bull. 1996, 37, 149.
25. Kennedy, J. P. Carbocation Polymerization; John Wiley & Sons: New York, 1982; p 31.
26. Gaylord, N. G.; Matyska, B. J. Polym. Sci., Part A-1 1966, 4, 2493.
27. Panek, J. S.; Jain, N. F. J. Org. Chem. 1993, 58, 2345.
28. Cope, A. C.; Hardy, E. M. J. Am. Chem. Soc. 1940, 62, 441.
29. When the reactions with separated 5e (22 mg, 0.11 mmol) and 6e (10 mg, 0.05 mmol) in 0.2 mL of pentane in the presence of aluminum chloride (10 mol % based on the amount of 5e and 6e used) and chlorotrimethylsilane (50 mol % based on the amount of 5e and 6e used) were carried out at room temperature for 2 h in NMR tubes, respectively, 5e gave 8R(S)-(trimethylsilyl)-1R(S),6R(S)-bicyclo[4.3.0]-non-2-ene (3e; 31%) and 3-(trimethylsilyl)propylbenzene (4e; 13%) and 6e gave polymeric materials. For 4e, see ref 27.
30. Jenkins, P. R.; Gut, R.; Wetter, H.; Eschenmoser, A. Helv. Chim. Acta 1979, 62, 1922.
31. Fleming, I.; Marchi, D.; Patel, K. J. Chem. Soc., Perkin Trans. 1 1981, 2518.
32. Musolf, M. C.; Speier, J. L. J. Org. Chem. 1964, 29, 2519.
33. Doucet, A. Ann. Sci. Univ. Besancon, Chim. 1979, 3; Chem. Abst. 1981, 95, 150745x.
34. Doucet, A. Ann. Sci. Univ. Besancon, Chim. 1979, 3; Chem. Abst. 1981, 95, 150745x.