R3Al-R′3SiOTf: Novel and powerful reagent system for stereospecific alkylation-silylation reactions of epoxides

Organic Letters

Volumn 5, Issue 18, 2003, Pages 3265-3268

  Shanmugam, Ponnusamy ^a   Miyashita, Masaaki ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EPOXIDE; REAGENT;

ALKYLATION; ARTICLE; SILYLATION; STEREOSPECIFICITY;

EID: 0141632756     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol035075x     Document Type: Article

References (29)

1. (a) Yamamoto, H. In Organometallics in Synthesis; Schlosser, M., Ed.; Wiley: Chichester, 2002; pp 535-578.
2. (b) For a review, see: Klunder, J. M.; Posner, G. H. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol.3, pp 207-239.
3. (c) Knight, D. W. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 3, pp 241-270.
4. (d) Garratt, P. J. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 3, pp 271-292.
5. (e) Sasaki, M.; Tanino, K.; Miyashita, M. Org. Lett. 2001, 3, 1765.
6. (f) Miyazawa, M.; Ishibashi, N.; Ohnuma, S.; Miyashita, M. Tetrahedron Lett. 1997, 38, 3419.
7. (a) Posner, G. H. Org. React. 1975, 22, 253-400.
8. (b) Lipshutz, B. H.; Sengupta, S. Org. React. 1992, 41, 135-631.
9. (c) Bonini, C.; Righi, G. Synthesis 1994, 225.
10. (d) Lipshutz, B. H.; Wilhelm, R. S.; Kozlowski, J. A.; Parker, D. J. Org. Chem. 1984, 49, 3928.
11. (e) Shiratani, T.; Kimura, K.; Yoshihara, K.; Hatakeyama, S.; Irie, H.; Miyashita, M. J. Chem. Soc., Chem. Commun. 1996, 21.
12. (f) Miyashita, M.; Shiratani, T.; Kawamine, K.; Hatakeyama, S.; Irie, H. J. Chem. Soc., Chem. Commun. 1996, 1027.
13. (a) Mole, T.; Jeffery, E. A. In Organoaluminum Compounds; Elsevier: Amsterdam, 1972.
14. (b) Negishi, E. In Organometallics in Organic Synthesis; Wiley: New York, 1980; Vol. 1, pp 286-393.
15. (c) Eisch, J. J. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon: Oxford, 1982; Vol. 1, pp 555-682.
16. (d) Negishi, E. Acc. Chem. Res. 1987, 20, 65.
17. (e) Maruoka, K.; Yamamoto, H. Tetrahedron 1988, 44, 5001.
18. (a) Suzuki, T.; Saimoto, H.; Tomioka, H.; Oshima, K.; Nozaki, H. Tetrahedron Lett. 1982, 23, 3597.
19. (b) Roush, W. R.; Adam, M. A.; Pesekis, S. M. Tetrahedron Lett. 1983, 24, 1377.
20. (a) Miyashita, M.; Hoshino, M.; Yoshikoshi, M. J. Org. Chem. 1991, 56, 6483.
21. (b) Ishibashi, N.; Miyazawa, M.; Miyashita, M. Tetrahedron Lett. 1998, 39, 377.
22. (a) Liu, C.; Hashimoto, Y.; Kudo, K.; Saigo, K. Bull. Chem. Soc., Jpn. 1996, 69, 2095.
23. (b) Sasaki, M.; Tanino, K.; Miyashita, M. J. Org. Chem. 2001, 66, 5388.
24. Abe, N.; Hanawa, H.; Maruoka, K.; Sasaki, M.; Miyashita, M. Tetrahedron Lett. 1999, 40, 5369.
25. (a) Zhou, H.; Campbell, E. J.; Nguyen, S. T. Org. Lett. 2001, 3, 2229.
26. (b) Schneider, C.; Brauner, J. Tetrahedron Lett. 2000, 41, 3043.
27. (c) Pfaltz, A.; Mattenberger, A. Angew. Chem., Int, Ed. Engl. 1982, 21, 71.
28. (d) Inghardt, T.; Frejd, T. Tetrahedron, 1991, 47, 6483.
29. 3N), followed by the same workup procedure, to afford the pure 5-methyl-oct-4-ol (93 mg, 91%).