Epoxydisilanes by direct double silylation of terminal epoxides

Synlett

Volumn , Issue 9, 2004, Pages 1610-1612

  Hodgson, David M ^a   Kirton, Eirene H M ^a  

^a UNIVERSITY OF OXFORD   (United Kingdom)

Author keywords

Carbenoids; Epoxides; Lithiation; Silylation; Sparteine

Indexed keywords

EPOXIDE; HEXANE; SILANE DERIVATIVE; SPARTEINE; TIN DERIVATIVE;

ARTICLE; LOW TEMPERATURE; SILYLATION;

EID: 3943058801     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-829083     Document Type: Article

References (22)

1. Hodgson, D. M.; Comina, P. J.; Drew, M. G. B. J. Chem. Soc., Perkin Trans. 1 1997, 2279.
2. (a) Page, P. C. B.; McKenzie, M. J. In Science of Synthesis: Houben-Weyl Methods of Molecular Transformations, Vol. 4; Fleming, I., Ed.; Thieme: Stuttgart, 2001, 513.
3. (b) Mattson, A. E.; Bharadwaj, A. R.; Scheidt, K. A. J. Am. Chem. Soc. 2004, 126, 2314.
4. (c) Linghu, X.; Potnick, J. R.; Johnson, J. S. J. Am. Chem. Soc. 2004, 126, 3070.
5. (a) Hodgson, D. M.; Norsikian, S. L. M. Org. Lett. 2001, 3, 461.
6. (b) See also: Hodgson, D. M.; Reynolds, N. J.; Coote, S. J. Tetrahedron Lett. 2002, 43, 7895.
7. (a) Eisch, J. J.; Galle, J. E. J. Am. Chem. Soc. 1976, 98, 4646.
8. (b) Burford, C.; Cooke, F.; Roy, G.; Magnus, P. Tetrahedron 1983, 39, 867.
9. (c) Eisch, J. J.; Galle, J. E. J. Organomet. Chem. 1988, 341, 293.
10. (d) Hudrlick, P. F.; Hudrlick, A. M. In Advances in Silicon Chemistry, Vol. 2; Larson, G. L., Ed.; JAI Press Inc.: Greenwich, 1993, 1.
11. (e) Courillon, C.; Marié, J.-C.; Malacria, M. Tetrahedron 2003, 59, 9759.
12. 2O as solvent were less effective in generating the desired epoxydisilane 1.
13. (a) Ukaji, Y.; Yoshida, A.; Fujisawa, T. Chem. Lett. 1990, 157.
14. (b) Agami, C.; Dechoux, L.; Doris, E.; Mioskowski, C. Tetrahedron Lett. 1997, 38, 4071.
15. For reviews, see: (a) Doris, E.; Dechoux, L.; Mioskowski, C. Synlett 1998, 337. (b) Hodgson, D. M.; Gras, E. Synthesis 2002, 1625.
16. For reviews, see: (a) Doris, E.; Dechoux, L.; Mioskowski, C. Synlett 1998, 337. (b) Hodgson, D. M.; Gras, E. Synthesis 2002, 1625.
17. Molander, G. A.; Mautner, K. J. Org. Chem. 1989, 54, 4042.
18. Preliminary investigations suggest LiCl aids the stability of the oxiranyl anion.
19. Epoxides in Table 1 were commercially available or prepared according to: (a) Elings, J. A.; Downing, R. S.; Sheldon, R. A. Eur. J. Org. Chem. 1999, 837; entry 3. (b) Rothberg, I.; Schneider, L.; Kirsch, S.; OFee, R. J. Org. Chem. 1982, 47, 2675; entry 4. (c) Yang, L.; Weber, A. E.; Greenlee, W. J.; Patchett, A. A. Tetrahedron Lett. 1993, 34, 7035; entry 5.
20. Epoxides in Table 1 were commercially available or prepared according to: (a) Elings, J. A.; Downing, R. S.; Sheldon, R. A. Eur. J. Org. Chem. 1999, 837; entry 3. (b) Rothberg, I.; Schneider, L.; Kirsch, S.; OFee, R. J. Org. Chem. 1982, 47, 2675; entry 4. (c) Yang, L.; Weber, A. E.; Greenlee, W. J.; Patchett, A. A. Tetrahedron Lett. 1993, 34, 7035; entry 5.
21. Epoxides in Table 1 were commercially available or prepared according to: (a) Elings, J. A.; Downing, R. S.; Sheldon, R. A. Eur. J. Org. Chem. 1999, 837; entry 3. (b) Rothberg, I.; Schneider, L.; Kirsch, S.; OFee, R. J. Org. Chem. 1982, 47, 2675; entry 4. (c) Yang, L.; Weber, A. E.; Greenlee, W. J.; Patchett, A. A. Tetrahedron Lett. 1993, 34, 7035; entry 5.
22. +] 329.2698.