Control of stereochemistry by σ-participation of a silyl group. A novel method for diastereoselective polyol synthesis

Journal of Organic Chemistry

Volumn 62, Issue 13, 1997, Pages 4206-4207

  Tanino, Keiji ^a   Yoshitani, Naoei ^a   Moriyama, Fumiko ^a   Kuwajima, Isao ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

POLYOL;

ARTICLE; DIASTEREOISOMER; DRUG STRUCTURE; DRUG SYNTHESIS; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION;

EID: 0030878776     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9703515     Document Type: Article

References (37)

1. (a) Wierschke, S. G.; Chandrasekhar, J.; Jorgensen, W. L. J. Am. Chem. Soc. 1985, 107, 1496.
2. (b) Lambert, J. B.; Wang, G.-t.; Finzel, R. B.; Teramura, D. H. Ibid. 1987, 109, 7838.
3. (c) Lambert, J. B.; Chelius, E. C. Ibid. 1990, 112, 8120.
4. (a) Colvin, E. Silicon in Organic Synthesis; Butterworths: London, 1981.
5. (b) Weber, W. P. Silicon Reagents for Organic Synthesis; Springer-Verlag: Berlin, 1983.
6. (c) Colvin, E. Silicon Reagents in Organic Synthesis; Academic Press: London, 1988.
7. (d) Fleming, I.; Dunoguès, J.; Smithers R. Org. React. 1989, 37, 57.
8. (a) Danheiser, R. L.; Dixon, B. R.; Gleason, R. W. J. Org. Chem. 1992, 57, 6094.
9. (b) Danheiser, R. L.; Takahashi, T.; Bertok, B.; Dixon, B. R. Tetrahedron Lett. 1993, 34, 3845.
10. (c) Knölker, H.-J.; Baum, G.; Graf, R. Angew. Chem. Int. Ed. Engl. 1994, 33, 1612.
11. (d) Kiyooka, S.; Shiomi, Y.; Kira, H.; Kaneko, Y.; Tanimori, S. J. Org. Chem. 1994, 59, 1958.
12. (e) Panek, J. S.; Jain, N. F. Ibid. 1994, 59, 2674.
13. (f) Monti, H.; Audran, G.; Léandri, G.; Monti, J.-P. Tetrahedron Lett. 1994, 35, 3073.
14. (g) Akiyama, T.; Ishikawa, K.; Ozaki, S. Chem. Lett. 1994, 627.
15. (h) Miura, K.; Okajima, S.; Hondo, T.; Hosomi, A. Tetrahedron Lett. 1995, 36, 1483.
16. (i) Dussault, P. A.; Zope, U. Ibid. 1995, 36, 3655 and references cited therein.
17. 3 via intramolecular trapping of a β-silyl cationic intermediate have been reported, it should be noted that few examples are known for the intermolecular version. For example, see: (a) Hayashi, T.; Okamoto, Y.; Kabeta, K.; Hagihara, T.; Kumada, M. J. Org. Chem. 1984, 49, 4224. (b) Hayashi, T.; Matsumoto, Y.; Morikawa, I.; Ito, Y. Tetrahedron: Asymmetry 1990, 1, 151.
18. 3 via intramolecular trapping of a β-silyl cationic intermediate have been reported, it should be noted that few examples are known for the intermolecular version. For example, see: (a) Hayashi, T.; Okamoto, Y.; Kabeta, K.; Hagihara, T.; Kumada, M. J. Org. Chem. 1984, 49, 4224. (b) Hayashi, T.; Matsumoto, Y.; Morikawa, I.; Ito, Y. Tetrahedron: Asymmetry 1990, 1, 151.
19. (a) Tamao, K.; Nakajima, T.; Sumiya, R.; Arai, H.; Higuchi, N.; Ito, Y. J. Am. Chem. Soc. 1986, 108, 6090.
20. (b) Bodnar, P. M.; Palmer, W. S.; Shaw, J. T.; Smitrovich, J. H.; Sonnenberg, J. D.; Presley, A. L.; Woerpel, K. A. J. Am. Chem. Soc. 1995, 117, 10575.
21. (c) Young, D. G. J.; Hale, M. R.; Hoveyda, A. H. Tetrahedron Lett. 1996, 37, 827.
22. Freeman, P. K.; Hutchinson, L. L. J. Org. Chem. 1980, 45, 1924.
23. (a) Marumoto, S.; Kuwajima, I. J. Am. Chem. Soc. 1993, 115, 9021.
24. (b) Behrens, K.; Kneisel, B. O.; Noltemeyer, M.; Brückner, R. Liebigs Ann. 1995, 385.
25. (a) Parker, R. E.; Isaacs, N. S. Chem. Rev. 1959, 59, 737.
26. (b) Rosowsky, A. in Heterocyclic Compounds with Three and Four-Membered Rings, Part I; Weissberger, A., Ed.; Interscience Publishers: New York, 1964; Chapter I.
27. (a) Stewart, J. J. P. J. Comput. Chem. 1989, 10, 209;
28. (b) 1989, 10, 211.
29. (a) Curci, R.; Fiorentino, M.; Troisi, L.; Edwards, J. O.; Pater, R. H. J. Org. Chem. 1980, 45, 4758.
30. (b) Cicala, G.; Curci, R.; Fiorentino, M.; Laricchiuta, O. Ibid. 1982, 47, 2670.
31. Guss, C. O.; Rosenthal, R. J. Am. Chem. Soc. 1955, 77, 2549.
32. The stereochemistry of the products was determined by NOE experiments.
33. Mundy, B. P. Concepts of Organic Synthesis; Marcel Dekker: New York, 1979; p 8.
34. (a) Tamao, K.; Kakui, T.; Iwahara, T.; Kanatani, R.; Yoshida, J.; Kumada, M. Tetrahedron 1983, 39, 983.
35. (b) Tamao, K. J. Synth. Org. Chem. 1988, 46, 861.
36. (c) Tamao, K.; Hayashi, T.; Ito, Y. Nihon Kagakukai Shi 1990, 509.
37. (d) Colvin, E. W. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 7, p 641.