Preference of 4-exo ring closure in copper-catalyzed intramolecular coupling of vinyl bromides with alcohols

Journal of the American Chemical Society

Volumn 129, Issue 26, 2007, Pages 8092-8093

  Fang, Yewen ^a   Li, Chaozhong ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL; ALLYL ALCOHOL; BROMIDE; COPPER; HETEROCYCLIC COMPOUND; LIGAND; PALLADIUM; UNCLASSIFIED DRUG; VINYL BROMIDE; VINYL DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; HECK REACTION; REACTION ANALYSIS; REACTION OPTIMIZATION; RING CLOSING METATHESIS; SYNTHESIS;

EID: 34447127018     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja072793w     Document Type: Article

References (21)

1. For reviews, see: (a) Kunz, K.; Scholz, U.; Ganzer, D. Synlett 2003, 2428.
2. (b) Ley, S. V.; Thomas, A. W. Angew. Chem., Int. Ed. 2003, 42, 5400.
3. (c) Beletskaya, I. P.; Cheprakov, A. V. Coord. Chem. Rev. 2004, 248, 2337.
4. (d) Dehli, J. R.; Legros, J.; Bolm, C. Chem. Commun. 2005, 973.
5. For the latest selected examples, see: (a) Toumi, M.; Couty, F.; Evano, G. Angew. Chem., Int. Ed. 2007, 46, 572.
6. (b) Okano, K.; Tokuyama, H.; Fukuyama, T. J. Am. Chem. Soc. 2006, 128, 7136.
7. (c) Cai, Q.; Zou, B.; Ma, D. Angew. Chem., Int. Ed. 2006, 45, 1276.
8. (a) Lu, H.; Li, C. Org. Lett. 2006, 8, 5365.
9. (b) Joyeau, R.; Kobaiter, R.; Sadet, J.; Wakselman, M. Tetrahedron Lett. 1989, 30, 337.
10. (a) Dollinger, L. M.; Howell, A. R. Bioorg. Med. Chem. Lett. 1998, 8, 977.
11. (b) Dollinger, L. M.; Howell, A. R. J. Org. Chem. 1998, 63, 6782.
12. (a) Howell, A. R.; Truong, A. Tetrahedron Lett. 1996, 37, 8651.
13. (b) Dollinger, L. M.; Howell, A. R. J. Org. Chem. 1996, 61, 7248.
14. (a) Fang, Y.; Li, C. Chem. Commun. 2005, 3574.
15. (b) Hu, T.; Li, C. Org. Lett. 2005, 7, 2035.
16. (c) Pan, Y.; Lu, H.; Fang, Y.; Fang, X.; Chen, L.; Qian, J.; Wang, J.; Li, C. Synthesis 2007, 1242.
17. Taillefer, M.; Ouali, A.; Renard, B.; Spindler, J. Chem. - Eur. J. 2006, 12, 5301.
18. (a) Nordmann, G.; Buchwald, S. L. J. Am. Chem. Soc. 2003, 125, 4978.
19. (b) Miyamoto, H.; Okawa, Y.; Nakazaki, A.; Kobayashi, S. Angew. Chem., Int. Ed. 2006, 45, 2274.
20. Grigg, R.; Stevenson, P.; Worakun, T. Tetrahedron 1988, 44, 2049.
21. Kuwabe, S.; Torraca, K. E.; Buchwald, S. L. J. Am. Chem. Soc. 2001, 123, 12202.