Use of chiral ionic liquids as solvents for the enantioselective photoisomerization of dibenzobicyclo[2.2.2]octatrienes

Organic Letters

Volumn 7, Issue 2, 2005, Pages 335-337

  Ding, Jie ^a   Desikan, Vasumathi ^a   Han, Xinxin ^a   Xiao, Tom L ^a   Ding, Rongfang ^a   Jenks, William S ^a   Armstrong, Daniel W ^a  

^a IOWA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; BENZENE DERIVATIVE; BICYCLO COMPOUND; METHANE; SOLVENT;

ARTICLE; ENANTIOSELECTIVITY; ISOMERIZATION; LIGHT; LIQUID; PHOTOLYSIS;

EID: 13444256295     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol047599i     Document Type: Article

References (31)

1. (a) Seebach, D.; Oei, H.-A. Angew. Chem., Int. Ed. Engl. 1975, 14, 634-636.
2. (b) Furia, F.-D.; Modena, G. Tetrahedron Lett. 1976, 50, 4637-4638.
3. (c) Laarhoven, W. H.; Cuppen, T. J. H. M. Chem. Commun. 1977, 47.
4. (d) Laarhoven, W. H.; Cuppen, T. J. H. M. J. Chem. Soc., Perkin Trans. 2 1978, 315-318 .
5. (a) Welton, T. Chem. Rev. 1999, 99, 2071-2084.
6. (b) Dupont, J.; de Souza, R. F.; Suarez, P. A. Z. Chem. Rev. 2002, 102, 3667-3692.
7. (c) Olivier-Bourbigou, H.; Magna, L. J. Mol. Catal. A: Chem. 2002, 182, 419-437.
8. (d) Baudequin, C.; Baudoux, J.; Levillain, J.; Cahard, D.; Gaumont, A.-C.; Plaquevent, J.-C. Tetrahedron: Asymmetry 2003, 14, 3081-3093.
9. (a) Sheldon, R. Chem. Commun. 2001, 2399-2407.
10. (b) Wasserscheid, P.; Keim, W. Angew. Chem., Int. Ed. 2000, 39, 3772-3789.
11. (c) Gordon, C. M. Appl. Catal. A: Gen. 2001, 222, 101-117.
12. Sheldon, R. A.; Lau, R. M.; Sorgedrager, M. J.; van Rantwijk, F.; Seddon, K. R. Green Chem. 2002, 4, 147-151.
13. (a) Huddleston, J. G.; Willauer, H. D.; Swatloski, R. P.; Visser, A. E.; Rogers, R. D. Chem. Commun. 1998, 1765-1766.
14. (b) Branco, L. C.; Crespo, J. G.; Afonso, C. A. M. Angew. Chem., Int. Ed. 2002, 41, 2771-2773.
15. (c) Armstrong, D. W.; He, L.; Liu, Y.-S. Anal. Chem. 1999, 71, 3873-3876.
16. (d) Armstrong, D. W.; Zhang, L.-K.; He, L.; Gross, M. L. Anal. Chem. 2001, 73, 3679-3686.
17. (e) Anderson, J. L.; Armstrong, D. W. Anal. Chem. 2003, 75, 4851-4858.
18. (f) Carda-Broch, S.; Berthod, A.; Armstrong, D. W. Rapid Commun. Mass Spectrom. 2003, 17, 553-560.
19. (g) Ding, J.; Welton, T.; Armstrong, D. W. Anal. Chem. 2004, 76, 6819-6822.
20. Pégot, B.; Vo-Thanh, G.; Gori, D.; Loupy, A. Tetrahedron Lett. 2004, 45, 6425-6428. Higher ee values have been obtained using more traditional chiral catalyst methods.
21. (a) Basavaiah, D.; Rao, A. J.; Satyanarayana, T. Chem. Rev. 2003, 103, 811-891.
22. (b) Markó, I. E.; Giles, P. R.; Hindley, N. J. Tetrahedron 1997, 53, 1015-1024.
23. (c) Oishi, T.; Oguri, H.; Hirama, M. Tetrahedron: Asymmetry 1995, 6, 1241-1244.
24. (d) Iwabuchi, Y.; Nakatani, M.; Yokoyama, N.; Hatakeyama, S. J. Am. Chem. Soc. 1999, 121, 10219-10220.
25. (e) Kawahara, S.; Nakano, A.; Esumi, T.; Iwabuchi, Y.; Hatakeyama, S. Org. Lett. 2003, 5, 3103-3105.
26. (f) Yang, K.-S.; Lee, W.-D.; Pan, J.-F.; Chen, K. J. Org. Chem. 2003, 68, 915-919.
27. Ciganek, E. J. Am. Chem. Soc. 1966, 88, 2882-2883.
28. Evans, S. V.; Garcia-Garibay, M.; Omkaram, N.; Scheffer, J. R.; Trotter, J.; Wireko, F. J. Am. Chem. Soc. 1986, 108, 5648-5650.
29. ILs 3 have been reported previously. Wasserscheid, P.; Bösmann, A.; Bolm, C. Chem. Commun. 2002, 200-201.
30. Samples were deoxygenated by flushing with Ar for about 10 min. Irradiation was from broadly emitting low-pressure fluorescent lamps whose output centers at 300 nm (RMR 3000 from Southern New England Ultraviolet). The initial concentration of 1 was 7-10 mM.
31. 4 aqueous solution at a flow rate of 1.0 mL/min.