Stereoselective hydroxycarbonylation of vinyl bromides to α,β-unsaturated carboxylic acids in the ionic liquid [BMIM]PF 6

Journal of Organic Chemistry

Volumn 71, Issue 10, 2006, Pages 3988-3990

  Zhao, Xiaodan ^a,b   Alper, Howard ^a   Yu, Zhengkun ^b  

^a UNIVERSITY OF OTTAWA   (Canada)

^b DALIAN INSTITUTE OF CHEMICAL PHYSICS   (China)

Author keywords

[No Author keywords available]

Indexed keywords

GEL COLUMN CHROMATOGRAGHY; IONIC LIQUIDS; MONOACIDS; STEREOSELECTIVE HYDROXYCARBONYLATION;

CARBONYLATION; CARBOXYLIC ACIDS; IONIZATION; ISOMERS; PROTONS; SALTS; SOLUTIONS; STEREOCHEMISTRY;

BROMINE COMPOUNDS;

BROMIDE; CARBONYL DERIVATIVE; CARBOXYLIC ACID; HYDROXYCARBONYL COMPOUND; IONIC LIQUID; SILICA GEL; UNCLASSIFIED DRUG; VINYL DERIVATIVE;

ARTICLE; CARBONYLATION; COLUMN CHROMATOGRAPHY; CRYSTALLIZATION; ISOMER; PROTON NUCLEAR MAGNETIC RESONANCE; PURIFICATION; STEREOCHEMISTRY;

CARBOXYLIC ACIDS; IMIDAZOLES; MOLECULAR STRUCTURE; VINYL COMPOUNDS;

EID: 33646519225     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo052651p     Document Type: Article

References (36)

1. Callow, R. K.; Johnston, N. C. Bee World 1960, 41, 152.
2. Cho, H.; Ueda, M.; Tamaoka, M.; Hamaguchi, M.; Aisaka, K.; Kiso, Y.; Inoue, T.; Ogino, R.; Tatsaoka, T.; Ishihara, T.; Noguchi, T.; Morita, I.; Murota, S. J. Med. Chem. 1991, 34, 1503.
3. Watanabe, T.; Hayashi, K.; Yoshimatsu, S.; Sakai, K.; Takeyma, S.; Takashima, K. J. Med. Chem. 1980, 23, 50.
4. For selected references, see: (a) Bellassoued, M.; Lensen, N.; Bakasse, M.; Mouelhi, S. J. Org. Chem. 1998, 63, 8785.
5. (b) Mogilaiah, K.; Reddy, G. R. Synth. Commun. 2004, 34, 205.
6. (c) Basavaiah, D.; Rao, A. J. Synth. Commun. 2002, 32, 195.
7. (a) Aoki, M.; Kaneko, M.; Izumi, S.; Ukai, K.; Iwasawa, N. J. Chem. Soc., Chem. Commun. 2004, 2568.
8. (b) Takimoto, M.; Shimizu, K.; Mori, M. Org. Lett. 2001, 3, 3345.
9. (a) Yamada, Y. M. A.; Takeda, K.; Takahashi, H.; Ikegami, S. Tetrahedron 2004, 60, 4097.
10. (b) Fukuyama, T.; Arai, M.; Matsubara, H.; Ryu, I. J. Org. Chem. 2004, 69, 8105.
11. (a) Miura, M.; Okuro, K.; Hattori, A.; Nomura, M. J. Chem. Soc., Perkin Trans. 1 1989, 73.
12. (b) Miura, M.; Shimoura, N.; Nomura, M. J. Chem. Soc., Perkin Trans. 1 1988, 1993.
13. (c) Miura, M.; Akase, F.; Shinohara, M.; Nomura, M. J. Chem. Soc., Perkin Trans. 1 1987, 1021.
14. Alper, H.; Amer, I.; Vasapollo, G. Terahedron Lett. 1989, 30, 2615.
15. For selected references, see: (a) Wasserscheid, P.; Keim, W. Angew. Chem., Int. Ed. 2000, 39, 3773.
16. (b) Dupont, J.; Souza, R. F. D.; Suarez, P. A. Z. Chem. Rev. 2002, 102, 3667.
17. (c) Xiao, J. C.; Twamley, B.; Shreeve, J. N. M. Org. Lett. 2004, 6, 3845.
18. (d) Cassol, C. C.; Umpierre, A. P.; Machado, G.; Wolke, S. I.; Dupont, J. J. Am. Chem. Soc. 2005, 127, 3298.
19. (e) Xiao, J. C.; Shreeve, J. N. M. J. Org. Chem. 2005, 70, 3072.
20. (f) Gholap, A. R.; Venkatesan, K.; Pasricha, R.; Daniel, T.; Lahoti, R. J.; Srinivasan, K. V. J. Org. Chem. 2005, 70, 4869.
21. (g) Wang, Z. M.; Bao, W. L.; Jiang, Y. J. Chem. Soc., Chem. Commun. 2005, 2849.
22. (h) Pegot, B.; Vo-Thanh. G. Synlett 2005, 9, 1409.
23. (i) Liao, M. C.; Duan, X. H.; Liang, Y. M. Tetrahedron Lett. 2005, 46, 3469.
24. (j) Guo, H. M.; Cun, L. F.; Gong, L. Z.; Mi, A. Q.; Jiang, Y. Z. J. Chem. Soc., Chem. Commun. 2005, 1450.
25. (k) Mu, X. D.; Meng, J. Q.; Li, Z. C.; Kou, Y. J. Am. Chem. Soc. 2005, 127, 9694.
26. (l) Qian, W. X.; Jin, E. L.; Bao, W. L.; Zhang, Y. M. Angew. Chem., Int. Ed. 2005, 44, 952.
27. (m) Mizushima, E.; Hayashi, T.; Tanaka, M. Top. Catal. 2004, 29, 163.
28. (n) Muller E.; Peczely, G.; Skoda-Foldes, R.; Takacs, E.; Kokotos, G.; Bellis, E.; Kollar, L. Tetrahedron 2005, 61, 797.
29. (o) Rangits, G.; Kollar, L. J. Mol. Catal. A: Chem. 2005, 242, 156.
30. (p) Zhao, D. B.; Fei, Z. F.; Geldbach, T. J.; Scopelliti, R.; Dyson, P. J. J. Am. Chem. Soc. 2004, 126, 15876.
31. (a) Park, S. B.; Alper, H. Org. Lett. 2003, 5, 3209.
32. (b) Park, S. B.; Alper, H. Tetrahedron Lett. 2004, 45, 5515.
33. (c) Park, S. B.; Alper, H. J. Chem. Soc., Chem. Commun. 2004, 1306.
34. (d) Park, S. B.; Alper, H. J. Chem. Soc., Chem. Commun. 2005, 1315.
35. After the reaction, the ionic liquid phase was extracted with diethyl ether. The solvent was dried under reduced pressure to give the crude residue. Compound 3a was isolated in 18% yield by preparative TLC plate, using hexane/AcOEt (5:1, v/v) as the developer.
36. Galamb, V.; Gopal, M.; Alper, H. Organometallics 1983, 2, 801.