An unusual and diastereoselective rearrangement during an intramolecular ene reaction involving a disilane

European Journal of Organic Chemistry

Volumn , Issue 26, 2013, Pages 5809-5813

  Giros, Audrey ^a   Guillot, Régis ^a   Blanco, Luis ^a   Deloisy, Sandrine ^a  

^a UNIVERSITÉ PARIS SUD   (France)

Author keywords

Cyclization; Diastereoselectivity; Ene reaction; Rearrangement; Silicon

Indexed keywords

EID: 84883560365     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.201300849     Document Type: Article

References (36)

1. A. Giros, Synlett 2012, 23, 805-806.
2. J. Robertson, G. O'Connor, D. S. Middleton, Tetrahedron Lett. 1996, 37, 3411-3414.
3. J. Robertson, G. O'Connor, T. Sardharwala, D. S. Middleton, Tetrahedron 2000, 56, 8309-8320.
4. S. Díez-González, R. Paugam, L. Blanco, Eur. J. Org. Chem. 2008, 3298-3307.
5. W. H. Campbell, T. K. Hilty, Eur. Pat. Appl. 0325248(A2), 1989.
6. E. Hengge, G. Bauer, E. Brandstätter, G. Kollmann, Monatsh. Chem. 1975, 106, 887-892.
7. M. Ishikawa, T. Fuchikami, M. Kumada, J. Organomet. Chem. 1976, 118, 139-153.
8. U. Herzog, G. Roewer, J. Organomet. Chem. 1997, 544, 217-223.
9. CCDC-921760 (for 11 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
10. Semi-empirical calculations were run with Spartan 08 (version 1.2), Molecular Modeling Package, Wavefunction, Inc., Irvine, CA, 2008.
11. K. Mikami, M. Shimizu, Chem. Rev. 1992, 92, 1021-1050.
12. H. M. R. Hoffmann, Angew. Chem. 1969, 81, 597-618;
13. Angew. Chem. Int. Ed. Engl. 1969, 8, 556-577.
14. J. Cai, A. G. Davies, J. Chem. Soc. Perkin Trans. 2 1992, 1743-1746.
15. A. Barbero, F. J. Pulido, M. C. Sañudo, ARKIVOC 2007, 4, 220-233.
16. J. B. Lambert, Tetrahedron 1990, 46, 2677-2689.
17. A. W. P. Jarvie, A. Holt, J. Thompson, J. Chem. Soc. B 1969, 852-855.
18. M. A. Cook, C. Eaborn, D. R. M. Walton, J. Organomet. Chem. 1970, 24, 301-306.
19. K. Schmohl, D. Wandschneider, H. Reinke, A. Heintz, H. Oehme, Eur. J. Inorg. Chem. 2002, 597-601.
20. A. C. Hopkinson, M. H. Lien, J. Org. Chem. 1981, 46, 998-1003.
21. Y. Apeloig, M. Karni, A. Stanger, H. Schwarz, T. Drewello, G. Czekay, J. Chem. Soc., Chem. Commun. 1987, 989-991.
22. T. Drewello, P. C. Burgers, W. Zummack, Y. Apeloig, H. Schwarz, Organometallics 1990, 9, 1161-1165.
23. R. Bakhtiar, C. M. Holznagel, D. B. Jacobson, J. Am. Chem. Soc. 1992, 114, 3227-3235.
24. K. Tamao, M. Kumada, J. Organomet. Chem. 1971, 30, 329-337.
25. G. Märkl, M. Horn, W. Schlosser, Tetrahedron Lett. 1986, 27, 4019-4022.
26. K. Sternberg, H. Oehme, Eur. J. Inorg. Chem. 1998, 177-181.
27. R. J. P. Corriu, G. Royo, J. Organomet. Chem. 1968, 14, 291-307.
28. R. J. P. Corriu, G. Royo, Bull. Soc. Chim. Fr. 1972, 1490-1497.
29. R. J. P. Corriu, F. Larcher, G. Royo, S. Olive, J. Organomet. Chem. 1976, 104, 161-171.
30. L. H. Sommer, C. L. Frye, G. A. Parker, K. W. Michael, J. Am. Chem. Soc. 1964, 86, 3271-3276.
31. A. G. Brook, W. W. Limburg, J. Am. Chem. Soc. 1963, 85, 832-833.
32. A. G. Brook, J. D. Pascoe, J. Am. Chem. Soc. 1971, 93, 6224-6227.
33. R. G. Daniels, L. A. Paquette, Organometallics 1982, 1, 1449-1453.
34. S. Bienz, A. Chapeaurouge, Helv. Chim. Acta 1991, 74, 1477-1488.
35. A. Chapeaurouge, S. Bienz, Helv. Chim. Acta 1993, 76, 1876-1889.
36. P. J. Coelho, L. Blanco, Eur. J. Org. Chem. 2000, 3039-3046.