First Direct Deprotonation-Electrophile Trapping of Simple Epoxides: Synthesis of α,β-Epoxysilanes from Terminal Epoxides

Organic Letters

Volumn 3, Issue 3, 2001, Pages 461-463

  Hodgson, David M ^a   Norsikian, Stephanie L M ^a  

^a UNIVERSITY OF OXFORD   (United Kingdom)

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EID: 0000914237     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol006948f     Document Type: Article

References (24)

1. Erden, I. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Eds.; Pergamon: Oxford, 1996; Vol. 1A, pp 97-171.
2. Eisch, J. J.; Galle, J. E. J. Am. Chem. Soc. 1976, 98, 4646-4648.
3. (a) Satoh, T. Chem. Rev. 1996, 96, 3303-3325.
4. (b) Mori, Y. Rev. Heteroat. Chem. 1997, 17, 183-210.
5. (a) Lohse, P., Loner, H.; Acklin, P.; Sternfeld, F.; Pfaltz, A. Tetrahedron Lett. 1991, 32, 615-618.
6. (b) Satoh, T.; Kobayashi, S.; Nakanishi, S.; Horigushi, K.; Irisa, S. Tetrahedron 1999, 55, 2515-2528.
7. Hodgson, D. M.; Lee, G. P.; Marriott, R. E.; Thompson, A. J.; Wisedale, R.; Witherington, J. J. Chem. Soc., Perkin Trans. 1 1998, 2151-2161.
8. Doris, E.; Dechoux, L.; Mioskowski, C. Synlett 1998, 337-343.
9. (7) Review: Hoppe, D.; Hense, T. Angew. Chem. 1997, 109, 2376-2410; Angew. Chem., Int. Ed. Engl. 1997, 36, 2282-2316.
10. Review: Hoppe, D.; Hense, T. Angew. Chem. 1997, 109, 2376-2410; Angew. Chem., Int. Ed. Engl. 1997, 36, 2282-2316.
11. (a) Bertini Gross, K. M.; Jun, Y. M.; Beak, P. J. Org. Chem. 1997, 62, 7679-7689.
12. (b) Harrison, J. R.; O'Brien, P.; Porter, D. W.; Smith, N. M. J. Chem. Soc., Perkin Trans. 1 1999, 3623-3631.
13. (c) Scheiber, P.; Nemes, P. Liebigs Ann. Chem. 1994, 1033-1036.
14. 32OSi 257.2300, found 257.2300.
15. 3SnCl, MeI) tried in situ were unsuccessful.
16. Hudrlik, P. F.; Hudrlick A. M. In Advances in Silicon Chemistry; Larson, G. L., Ed.; JAI: Greenwich, 1993; Vol. 2, pp 1-89.
17. (12) 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, 837-846 (entry 3). (b) Yang, L.; Weber, A. E.; Greenlee, W. J.; Patchett, A. A. Tetrahedron Lett. 1993, 34, 7035-7038 (entry 4). (c) Rothberg, I.; Schneider, L.; Kirsch, S.; OFee, R. J. Org. Chem. 1982, 47, 2675-2676 (entry 5). (d) Michnick, T. J.; Matteson, D. S. Synlett 1991, 631-632 (entries 6-7).
18. 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, 837-846 (entry 3). (b) Yang, L.; Weber, A. E.; Greenlee, W. J.; Patchett, A. A. Tetrahedron Lett. 1993, 34, 7035-7038 (entry 4). (c) Rothberg, I.; Schneider, L.; Kirsch, S.; OFee, R. J. Org. Chem. 1982, 47, 2675-2676 (entry 5). (d) Michnick, T. J.; Matteson, D. S. Synlett 1991, 631-632 (entries 6-7).
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, 837-846 (entry 3). (b) Yang, L.; Weber, A. E.; Greenlee, W. J.; Patchett, A. A. Tetrahedron Lett. 1993, 34, 7035-7038 (entry 4). (c) Rothberg, I.; Schneider, L.; Kirsch, S.; OFee, R. J. Org. Chem. 1982, 47, 2675-2676 (entry 5). (d) Michnick, T. J.; Matteson, D. S. Synlett 1991, 631-632 (entries 6-7).
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, 837-846 (entry 3). (b) Yang, L.; Weber, A. E.; Greenlee, W. J.; Patchett, A. A. Tetrahedron Lett. 1993, 34, 7035-7038 (entry 4). (c) Rothberg, I.; Schneider, L.; Kirsch, S.; OFee, R. J. Org. Chem. 1982, 47, 2675-2676 (entry 5). (d) Michnick, T. J.; Matteson, D. S. Synlett 1991, 631-632 (entries 6-7).
21. Molander, G. A.; Mautner, K. J. Org. Chem. 1989, 54, 4042-4050.
22. (a) Burford, C.; Cook, F.; Roy, G.; Magnus, P. Tetrahedron 1983, 39, 867-876 (entry 6).
23. (b) Warren, J. D.; Shi, Y. J. Org. Chem. 1999, 64, 7675-7677 (entry 7).
24. Tokunaga, M.; Larrow, J. F.; Kakiuchi, F.; Jacobsen, E. N. Science 1997, 277, 936-938.