Selective synthesis of functionalized, tertiary silanes by diastereoselective rearrangement-addition

Organic Letters

Volumn 7, Issue 22, 2005, Pages 4911-4913

  Trost, Barry M ^a   Ball, Zachary T ^a   Kang, Eun Joo ^a  

^a STANFORD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

SILANE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

MOLECULAR STRUCTURE; SILANES; STEREOISOMERISM;

EID: 27644529802     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0518636     Document Type: Article

References (30)

1. Colvin, E. W. Silicon in Organic Synthesis; Butterworth: London, 1981.
2. Fleming, I.; Barbero, A.; Walter, D. Chem. Rev. 1997, 97, 2063-2192.
3. Jones, G. R.; Landais, Y. Tetrahedron 1996, 52, 7599-7662.
4. (a) Oi, S.; Honma, Y.; Inoue, Y. Org. Lett. 2002, 4, 667-669.
5. (b) Oi, S.; Taira, A.; Honma, Y.; Inoue, Y. Org. Lett. 2003, 5, 97-99.
6. (c) Hiyama, T. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P., Eds.; Wiley-VCH: Weinheim, Germany, 1998.
7. (d) Denmark, S. E.; Ober, M. H. Aldrichimica Acta 2003, 36, 75-85.
8. (e) Denmark, S. E.; Sweis, R. F. Acc. Chem. Res. 2002, 35, 835-846.
9. (a) Ishikawa, T.; Kudo, T.; Shigemori, K.; Saito, S. J. Am. Chem. Soc. 2000, 122, 7633-7637.
10. (b) Stork, G.; Chan, T. Y.; Breault, G. A. J. Am. Chem. Soc. 1992, 114, 7578-7579.
11. (c) Langkopf, E.; Schinzer, D. Chem. Rev. 1995, 95, 1375-1408.
12. Hiyama, T.; Kusumoto, T. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 8, pp 763-792.
13. Trost, B. M.; Ball, Z. T. Synthesis 2005, 853-887.
14. (a) Trost, B. M.; Ball, Z. T.; Laemmerhold, K. M. J. Am. Chem. Soc. 2005, 127, 10028-10038.
15. (b) Trost, B. M.; Ball, Z. T.; Jöge, T. Angew. Chem., Int. Ed. 2003, 42, 3415-3418.
16. Hasan, I.; Kishi, Y. Tetrahedron Lett. 1980, 21, 4229-4232.
17. Hanson, R. M. Chem. Rev. 1991, 91, 437-475.
18. Other reactions of epoxysilanes: (a) Hudrlik, P. F.; Hudrlik, A. M.; Rona, R. J.; Misra, R. N.; Withers, G. P. J. Am. Chem. Soc. 1977, 99, 1993-1996.
19. (b) Hudrlik, P. F.; Hudrlik, A. M.; Misra, R. N.; Peterson, D.; Withers, G. P.; Kulkarni, A. K. J. Org. Chem. 1980, 45, 4444-4448.
20. (c) Hudrlik, P. F.; Hudrlik, A. M. Advances in Silicon Chemistry; JAI Press: Greenwich, CT, 1993; Vol. 2, pp 1-89.
21. (d) Hudrlik, P. F.; Ma, D.; Bhamidipati, R. S.; Hudrlik, A. M. J. Org. Chem. 1996, 61, 8655-8658.
22. (a) Jung, M. E.; Damico, D. C. J. Am. Chem. Soc. 1995, 117, 7379-7388.
23. (b) Jung, M. E.; Anderson, K. L. Tetrahedron Lett. 1997, 38, 2605-2608.
24. (c) Maruoka, K.; Ooi, T.; Nagahara, S.; Yamamoto, H. Tetrahedron 1991, 47, 6983-6998.
25. (d) Matsubara, S.; Yamamoto, H.; Oshima, K. Angew. Chem., Int. Ed. 2002, 41, 2837-2840.
26. (a) Crudden, C. M.; Alper, H. J. Org. Chem. 1994, 59, 3091-3097.
27. (b) Enders, D.; Lohray, B. B.; Burkamp, F.; Bhushan, V.; Hett, R. Liebigs Ann. Chem. 1996, 189-200.
28. (c) Chauret, D. C.; Chong, J. M.; Ye, Q. Tetrahedron: Asymmetry 1999, 10, 3601-3614.
29. (d) Duhamel, L.; Gralak, J.; Bouyanzer, A. Chem. Commun. 1993, 1763-1765.
30. Weber, W. P. Silicon Reagents for Organic Synthesis; Springer-Verlag: Berlin 1983; Chapter 6, pp 58-78.