Direct and facile bromination at the 5- and 5′-positions of (R)-6,6′-dialkyl-and (R)-6,6′-diaryl-2,2′-binaphthols

Synlett

Volumn , Issue 6, 2008, Pages 853-856

  Zhang, Shuwei ^a   Liu, Yan ^a   Huang, Hui ^a   Zheng, Lifei ^a   Wu, Linglin ^a   Cheng, Yixiang ^a  

^a NANJING UNIVERSITY   (China)

Author keywords

(R) BINOL, bromination; Five step reaction

Indexed keywords

5,5' DIBROMO 6,6' BIS(4 METHYLPHENYL) 2,2' BINAPHTHOL; 5,5' DIBROMO 6,6' BIS(4 TRIFLUROMETHYLPHENYL) 2,2' BINAPHTHOL; 5,5' DIBROMO 6,6' DIBUTYL 2,2' BINAPHTHOL; 5,5' DIBROMO BIS(3,5 DIMETHYPHENYL) 2,2' BINAPHTHOL; NAPHTHOL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BROMINATION; CHEMICAL REACTION;

EID: 42149147380     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2008-1042902     Document Type: Article

References (37)

1. (a) Brunel, J. M. Chem. Rev. 2005, 105, 857.
2. (b) Pu, L. Chem. Rev. 2004, 104, 1687.
3. (c) Takizawa, S.; Somei, H.; Jayaprakash, D.; Sasai, H. Angew. Chem. Int. Ed. 2003, 42, 5711.
4. (d) Casas, J.; Nájera, C.; Sansano, J. M.; Saá, J. M. Tetrahedron 2004, 60, 10487.
5. (a) Noyori, R. Chem. Soc. Rev. 1989, 18, 187.
6. (b) Noyori, R.; Kitamura, M. Angew. Chem., Int. Ed. Engl. 1991, 30, 49.
7. (a) Cox, P. J.; Wang, W.; Snieckus, V. Tetrahedron Lett. 1992, 33, 2253.
8. (b) Sogah, G. D. Y.; Cram, D. J. J. Am. Chem. Soc. 1979, 101, 3035.
9. (c) Minatti, A.; Doetz, K. H. Tetrahedron: Asymmetry 2005, 16, 3256.
10. (d) Xu, Y. J.; Clarkson, G. C.; Docherty, G.; North, C. L.; Woodward, G.; Wills, M. J. Org. Chem. 2005, 70, 8079.
11. (e) Shi, M.; Chen, L. H.; Li, C. Q. J. Am. Chem. Soc. 2005, 127, 3790.
12. (f) Zimmer, R.; Schefzig, L.; Peritz, A.; Dekaris, V.; Reissig, H. U. Synthesis 2004, 1439.
13. (g) Wu, T. R.; Shen, L.; Chong, J. M. Org. Lett. 2004, 6, 2701.
14. (a) Shimada, T.; Suda, M.; Nagano, T.; Kakiuchi, K. J. Org. Chem. 2005, 70, 10178.
15. (b) Alame, M.; Jahjah, M.; Berthod, M.; Lemaire, M.; Meille, V.; Bellefon, C. J. Mol. Catal. A: Chem. 2007, 268, 205.
16. (c) Pirkle, W. H.; Schreiner, J. L. J. Org. Chem. 1981, 46, 4988.
17. (a) Tian, Y.; Yang, Q. C.; Mak, T. C. W.; Chan, K. S. Tetrahedron 2002, 58, 3951.
18. (b) Tian, Y.; Chan, K. S. Tetrahedron Lett. 2000, 41, 8813.
19. (c) Hu, Q. S.; Pugh, V.; Sabat, M.; Pu, L. J. Org. Chem. 1999, 64, 7528.
20. (a) Lee, S. J.; Lin, W. B. J. Am. Chem. Soc. 2002, 124, 4554.
21. (b) Lee, S. J.; Hu, A.; Lin, W. B. J. Am. Chem. Soc. 2002, 124, 12948.
22. (c) Zhu, Y. L.; Gergel, N.; Majumdar, N.; Harriott, L. R.; Bean, J. C.; Pu, L. Org. Lett. 2006, 8, 355.
23. (d) Cui, Y.; Ewans, O. R.; Ngo, H. L.; White, P. S.; Lin, W. Angew. Chem. Int. Ed. 2002, 41, 1159.
24. (a) Ishitani, H.; Ueno, M.; Kobayashi, S. J. Am. Chem. Soc. 2000, 122, 8180.
25. (b) Kumaraswamy, G.; Sastry, M. N. V.; Jena, N.; Kumarb, K. R.; Vairamanic, M. Tetrahedron: Asymmetry 2003, 14, 3797.
26. (c) Chin, J.; Kim, D. C.; Kim, H.-J.; Panosyan, F. B.; Kim, K. M. Org. Lett. 2004, 6, 2591.
27. (d) Yamashita, Y.; Ishitani, H.; Shimizu, H.; Kobayashi, S. J. Am. Chem. Soc. 2002, 124, 3292.
28. (e) Shigeki, M.; Takashi, O.; Shibasaki, M. Tetrahedron Lett. 2000, 41, 8473.
29. (a) Lloyd, D. G.; Hughes, R. B.; Zisterer, D. M.; Williams, D. C.; Fattorusso, C.; Catalanotti, B.; Campiani, G.; Meegan, M. J. J. Med. Chem. 2004, 47, 5612.
30. (b) Norrild, J. C.; Eggert, H. J. Am. Chem. Soc. 1995, 117, 1479.
31. (c) Qu, D. H.; Chun, Q. W.; Ren, J.; Tian, H. Org. Lett. 2004, 6, 2085.
32. (d) Morgan, J.; Pinhey, J. T. J. Chem. Soc. 1990, 3, 715.
33. (a) Sonogashira, K. J. Organomet. Chem. 2002, 46, 653.
34. (b) Ma, L.; Hu, Q. S.; Musick, K. Y.; Wu, C.; Kwan, C. M. S.; Pu, L. Macromolecules 1996, 29, 5083.
35. (c) Alami, M.; Linstrumelle, G. Tetrahedron Lett. 1991, 32, 6109.
36. (d) Liu, Y.; Zong, L. L.; Zheng, L. F.; Wu, L. L.; Cheng, Y. X. Polymer 2007, 48, 6799.
37. -1.