Regioselective lithiation/retro-Brook rearrangement via direct deprotonation

Tetrahedron

Volumn 69, Issue 2, 2013, Pages 559-563

  He, Yongping ^a   Hu, Haitao ^a   Xie, Xingang ^a   She, Xuegong ^a,b  

^a LANZHOU UNIVERSITY   (China)

^b LANZHOU INSTITUTE OF CHEMICAL PHYSICS   (China)

Author keywords

Benzyl silanes; Direct deprotonation; Retro Brook rearrangement; Vinyl silanes

Indexed keywords

SILANE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CROSS REACTION; DEPROTONATION; LITHIATION; PRIORITY JOURNAL;

EID: 84878244812     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2012.11.024     Document Type: Article

References (40)

1. (a) Chan, T. H. Chem. Rev. 1995, 95, 1279-1292;
2. (b) Panek, J. S. Chem. Rev. 1995, 95, 1293-1316;
3. (c) Keith, A. H. Chem. Rev. 1995, 95, 1317-1350;
4. (d) Schinzer, D. Chem. Rev. 1995, 95, 1351-1408;
5. (e) Denmark, S. E. Angew. Chem., Int. Ed. 2010, 49, 2978-2986 and references cited therein;
6. (f) Oestreich, M. Chem. Commun. 2011, 7917-7932.
7. (a) Denmark, S. E. J. Am. Chem. Soc. 1999, 121, 5821-5822;
8. (b) Yoshida, J. J. Am. Chem. Soc. 2001, 123, 11577-11585;
9. (c) Trost, B. M. Org. Lett. 2003, 5, 1895-1898;
10. (d) Anderson, J. C. J. Org. Chem. 2004, 69, 8971-8974;
11. (e) Hiyama, T. J. Am. Chem. Soc. 2005, 127, 6952-6953.
12. (a) Toshikazu, H.; Takashi, F.; Yoshiki, O. Tetrahedron Lett. 1994, 35, 8005-8008;
13. (b) Toshikazu, H. Coord. Chem. Rev. 2003, 237, 271-279.
14. (a) Lautens, M.; Delanghe, P. H. M.; Goh, J. B.; Zhang, C. H. J. Org. Chem. 1992, 57, 3270-3272;
15. (b) Marumoto, S.; Kuwajima, I. J. Am. Chem. Soc. 1993, 115, 9021-9024;
16. (c) Bousbaa, J.; Ooms, F.; Krief, A. Tetrahedron Lett. 1997, 38, 7625-7628;
17. (d) Sammtleben, F.; Noltemeyer, M.; BrJckner, R. Tetrahedron Lett. 1997, 38, 3893-3896.
18. (a) Brook, A. G.; Pascoe, J. D. J. Am. Chem. Soc. 1971, 93, 6224-6227;
19. (b) Brook, A. G. Acc. Chem. Res. 1974, 7, 77-84.
20. (b) Whisler, M. C.; Snieckus, V.; Beak, P. Angew. Chem., Int. Ed. 2004, 43, 2206-2225 and references cited therein.
21. (a) Wittig, G.; Pockels, U. Chem. Ber. 1938, 71, 1903-1912;
22. (b) Gilman, H.; Langham, W.; Jacoby, A. L. J. Am. Chem. Soc. 1939, 61, 106-109.
23. (a) Snieckus, V. Chem. Rev. 1990, 90, 879-933;
24. (b) Tilly, D.; Fu, J.; Zhao, B.; Alessi, M.; Snieckus, V.; Mortier, J. Org. Lett. 2010, 12, 68-71;
25. (c) Miller, R. E.; Snieckus, V. Org. Lett. 2010, 12, 2198-2201.
26. O'Shea, D. F. J. Am. Chem. Soc. 2009, 131, 3142-3143.
27. (a) Winter, E.; BrJckner, R. Synlett 1994, 12, 1049-1053;
28. (b) Jiang, X.-L.; Bailey, W. F. Organometallics 1995, 14, 5704-5707;
29. (c) Kleinfeld, S. H.; Wegelius, E.; Hoppe, D. Helv. Chim. Acta 1999, 82, 2413-2424;
30. (d) Simpkins, S. M. E.; Kariuki, B. M.; Arico, C. S.; Cox, L. R. Org. Lett. 2003, 5, 3971-3974;
31. (e) Nahm, M. R.; Johnson, J. S. Angew. Chem., Int. Ed. 2005, 44, 2377-2379;
32. (f) Yamago, S.; Fujita, K.; Miyoshi, M.; Kotani, M.; Yoshida, J. Org. Lett. 2005, 7, 909-911;
33. (g) Nakazaki, A.; Nakai, T.; Tomooka, K. Angew. Chem., Int. Ed. 2006, 45, 2235-2238;
34. (h) Mori, H.; Matsuo, T.; Yoshioka, Y.; Katsumura, S. J. Org. Chem. 2006, 71, 9004-9012;
35. (i) Mori, Y.; Futamura, Y.; Horisaki, K. Angew. Chem., Int. Ed. 2008, 47, 1091-1093.
36. (2-Bromo-4,6-dimethylphenoxy)(tert-butyl)dimethylsilane gave 21% 4b0 and 40% another product that silyl group shift at the aromatic ring. Although 2-bromo-6-((tert-butyldimethylsilyl)methyl)-4-methylphenol 4b0 would be obtained by general procedures from 4b. References about silyl group shifting at the aromatic ring see: (a) Comanita, B. M.; Woo, S.; Fallis, A. G. Tetrahedron Lett. 1999, 40, 5283-5286;
37. (b) Thadani, A. N.; Huang, Y.; Rawal, V. H. Org. Lett. 2007, 9, 3873-3876.
38. (a) Smith, A. B., III. Acc. Chem. Res. 2004, 37, 365-377;
39. (b) Smith, A. B., III. J. Am. Chem. Soc. 2006, 128, 66-67;
40. (c) Smith, A. B., III. J. Am. Chem. Soc. 2006, 128, 12368-12369.