Ionic liquids and chirality: Opportunities and challenges

Tetrahedron Asymmetry

Volumn 14, Issue 20, 2003, Pages 3081-3093

  Baudequin, Christine ^a   Baudoux, Jérome ^a   Levillain, Jocelyne ^b   Cahard, Dominique ^a   Gaumont, Annie Claude ^b   Plaquevent, Jean Christophe ^a  

^a Normandie Université   (France)

^b UNIVERSITÉ DE CAEN   (France)

Author keywords

[No Author keywords available]

Indexed keywords

CYANOHYDRIN; IONIC LIQUID; UNCLASSIFIED DRUG;

ALDOL REACTION; ALLYLATION; ASYMMETRIC CATALYSIS; ASYMMETRIC SYNTHESIS; BIOCATALYST; CHIRALITY; CYCLOPROPANATION; DIHYDROXYLATION; EPOXIDATION; FLUORINATION; HYDROGENATION; LIQUID; MANNICH REACTION; PRIORITY JOURNAL; REVIEW; RING OPENING;

EID: 0345076940     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(03)00596-2     Document Type: Review

References (71)

1. Freemantle, M. C&E News, August 24, 1998, p. 32; May 15, 2000, p. 37; January 1, 1999, p. 9.
2. Freemantle, M. C&E News, August 24, 1998, p. 32; May 15, 2000, p. 37; January 1, 1999, p. 9.
3. Freemantle, M. C&E News, August 24, 1998, p. 32; May 15, 2000, p. 37; January 1, 1999, p. 9.
4. Carmichael, H. Chem. Brit., January 2000, p. 36.
5. Holbrey J.D., Seddon K.R. Clean Prod. Processes. 1:1999;223.
6. For reviews, see: (a) Welton, T. Chem. Rev. 1999, 99, 2071-2083; (b) Dupont, J.; de Souza, R. F.; Suarez, P. A. Z. Chem. Rev. 2002, 102, 3667-3692; (c) Olivier-Bourbigou, H.; Magna, L.; J. Mol. Cat. A: Chem. 2002, 3484, 1-19.
7. For reviews, see: (a) Welton, T. Chem. Rev. 1999, 99, 2071-2083; (b) Dupont, J.; de Souza, R. F.; Suarez, P. A. Z. Chem. Rev. 2002, 102, 3667-3692; (c) Olivier-Bourbigou, H.; Magna, L.; J. Mol. Cat. A: Chem. 2002, 3484, 1-19.
8. For reviews, see: (a) Welton, T. Chem. Rev. 1999, 99, 2071-2083; (b) Dupont, J.; de Souza, R. F.; Suarez, P. A. Z. Chem. Rev. 2002, 102, 3667-3692; (c) Olivier-Bourbigou, H.; Magna, L.; J. Mol. Cat. A: Chem. 2002, 3484, 1-19.
9. For other reviews, see: (a) Sheldon, R. Chem. Commun. 2001, 2399-2407; (b) Wasserscheid, P.; Keim, W. Angew. Chem., Int. Ed. Engl. 2000, 39, 3772-3789; (c) Gordon, C. M. Appl. Catal. A: Gen. 2001, 222, 101-117; (d) Dyson, P. J. Transition Met. Chem. 2002, 27, 353-358.
10. For other reviews, see: (a) Sheldon, R. Chem. Commun. 2001, 2399-2407; (b) Wasserscheid, P.; Keim, W. Angew. Chem., Int. Ed. Engl. 2000, 39, 3772-3789; (c) Gordon, C. M. Appl. Catal. A: Gen. 2001, 222, 101-117; (d) Dyson, P. J. Transition Met. Chem. 2002, 27, 353-358.
11. For other reviews, see: (a) Sheldon, R. Chem. Commun. 2001, 2399-2407; (b) Wasserscheid, P.; Keim, W. Angew. Chem., Int. Ed. Engl. 2000, 39, 3772-3789; (c) Gordon, C. M. Appl. Catal. A: Gen. 2001, 222, 101-117; (d) Dyson, P. J. Transition Met. Chem. 2002, 27, 353-358.
12. For other reviews, see: (a) Sheldon, R. Chem. Commun. 2001, 2399-2407; (b) Wasserscheid, P.; Keim, W. Angew. Chem., Int. Ed. Engl. 2000, 39, 3772-3789; (c) Gordon, C. M. Appl. Catal. A: Gen. 2001, 222, 101-117; (d) Dyson, P. J. Transition Met. Chem. 2002, 27, 353-358.
13. Sheldon R.A., Lau R.M., Sorgedrager M.J., van Rantwijk F., Seddon K.R. Green Chem. 4:2002;147-151.
14. Loh T.P., Feng L.C., Yang H.Y., Yang J.Y. Tetrahedron Lett. 43:2002;8741-8743.
15. Kotrusz P., Kmentová I., Gotov B., Toma S., Solcá niová E. Chem. Commun. 2002;2510-2511.
16. Kitazume T., Jiang Z., Kasai K., Mihara Y., Suzuki M. J. Fluorine Chem. 121:2003;205-212.
17. McCluskey A., Garner J., Young D.J., Caballero S. Tetrahedron Lett. 41:2000;8147-8151.
18. Chen S.L., Ji S.J., Loh T.P. Tetrahedron Lett. 44:2003;2405-2408.
19. Baudequin C., Plaquevent J.-C., Audouard C., Cahard D. Green Chem. 4:2002;584-586.
20. Tzschuche C.C., Market C., Bannwarth W., Roller S., Hebel A., Haag R. Angew. Chem., Int. Ed. Engl. 41:2002;3964-4000.
21. Chauvin Y., Mussmann L., Olivier H. Angew. Chem., Int. Ed. Engl. 34:1995;2698-2700.
22. Berger A., de Souza R.F., Delgado M.R., Dupont J. Tetrahedron: Asymmetry. 12:2001;1825-1828.
23. Guernik S., Wolfson A., Herskowitz M., Greenspoon N., Geresh S. Chem. Commun. 2001;2314-2315.
24. Monteiro A.L., Zinn F.K., de Souza R.F., Dupont J. Tetrahedron: Asymmetry. 8:1997;177-179.
25. Brown R.A., Pollet P., McKoon E., Eckert C.A., Liotta C.L., Jessop P.G. J. Am. Chem. Soc. 123:2001;1254-1255.
26. Jessop P.G., Stanley R.R., Brown R.A., Eckert C.A., Liotta C.L., Ngo T.T., Pollet P. Green Chem. 5:2003;3-8.
27. Wolfson A., Vankelecom I.F.J., Jacobs P.A. Tetrahedron Lett. 44:2003;1195-1198.
28. Baleizão C., Gigante B., Garcia H., Corma A. Green Chem. 4:2002;272-274.
29. Fraile J.M., Garciã J.I., Herrerias C.I., Mayoral J.A., Carrié D., Vaultier M. Tetrahedron: Asymmetry. 12:2001;1891-1894.
30. Toma S., Gotov B., Kmentová I., Solcániová E. Green Chem. 2:2000;149-151.
31. Song C.E., Oh C.R., Roh E.J., Choo D.J. Chem. Commun. 2000;1743-1744.
32. Oh C.R., Choo D.J., Shim W.H., Lee D.H., Roh E.J., Lee S.-g., Song C.E. Chem. Commun. 2003;1100-1101.
33. Song C.E., Roh E.J. Chem. Commun. 2000;837-838.
34. Branco L.C., Afonso C.A.M. Chem. Commun. 2002;3036-3037.
35. Song C.E., Jung D-u., Roh E.J., Lee S.-g., Chi D.Y. Chem. Commun. 2002;3038-3039.
36. Sheldon R.A., Lau R.M., Sorgedrager M.J., van Rantwijk F., Seddon K.R. Green Chem. 4:2002;147-151.
37. Kragl U., Eckstein M., Kaftzik N. Curr. Opin. Biotechnol. 13:2002;565-571.
38. van Rantwijk F., Lau R.M., Sheldon R.A. Trends Biotechnol. 21:2003;131-138.
39. Itoh T., Akasaki E., Kudo K., Shirakami S. Chem. Lett. 2001;262-263.
40. Itoh T., Akasaki E., Nishimura Y. Chem. Lett. 2002;154-155.
41. Eckstein M., Wasserscheid P., Kragl U. Biotechnol. Lett. 24:2002;763-767.
42. Schöfer S.H., Kaftzik N., Wasserscheid P., Kragl U. Chem. Commun. 2001;425-426.
43. Lozano P., de Diego T., Carrié D., Vaultier M., Iborra J.L. Biotechnol. Prog. 19:2003;380-382.
44. Park S., Kazlauskas R.J. J. Org. Chem. 66:2001;8395-8401.
45. Lozano P., de Diego T., Carrié D., Vaultier M., Iborra J.L. Chem. Commun. 2002;692-693.
46. Reetz M.T., Wiesenhöfer W., Franciò G., Leitner W. Chem. Commun. 2002;992-993.
47. Kim K-W., Song B., Choi M-Y., Kim M.-J. Org. Lett. 3:2001;1507-1509.
48. Lee J.K., Kim M.-J. J. Org. Chem. 67:2002;6845-6847.
49. Kielbasinski P., Albrycht M., Luczak J., Mikolajczyk M. Tetrahedron: Asymmetry. 13:2002;735-738.
50. Zhao H., Luo R.G., Malhotra S.V. Biotechnol. Progress. 19:2003;1016-1018.
51. Zhao H., Malhotra S.V. Biotechnol. Lett. 24:2002;1257-1259.
52. Howarth J., James P., Dai J. Tetrahedron Lett. 42:2001;7517-7519.
53. March J. Advanced Organic Chemistry. 1977;106-108 McGraw-Hill, New York.
54. For a review of NMR chiral solvating agent, see: Pirkle W.H., Hoover D.J. Top. Stereochem. 13:1982;263-331.
55. For NMR databases in chiral solvents, see: Kobayashi Y., Hayashi N., Kishi Y. Org. Lett. 4:2002;411-414. and references cited therein.
56. Seebach D., Oei H.A. Angew. Chem., Int. Ed. Engl. 14:1975;634-636.
57. Ulbert O., Szarka Á., Halasi S., Somogyi B., Bélafi- Bakó K., Gubicza L. Biotechnol. Techn. 13:1999;299-302.
58. Dupont J., Suarez P.A.Z., de Souza R.F., Burrow R.A., Kintzinger J.P. Chem. Eur. J. 6:2000;2377-2381.
59. Hagiwara R., Ito Y. J. Fluorine Chem. 105:2000;221-227.
60. Schröder U., Wadhawan J.D., Compton R.G., Marken F., Suarez P.A.Z., Consorti C.S., de Souza R.F., Dupont J. New J. Chem. 24:2000;1009-1015.
61. Aggarwal A., Lancaster N.L., Sethi A.R., Welton T. Green Chem. 4:2002;517-520.
62. Earle M.J., McCormac P.B., Seddon K.R. Green Chem. 1:1999;23-25.
63. Howarth J., Hanlon K., Fayne D., McCormac P. Tetrahedron Lett. 38:1997;3097-3100.
64. Bao W., Wang Z., Li Y. J. Org. Chem. 68:2003;591-593.
65. Wasserscheid P., Bösmann A., Bolm C. Chem. Commun. 2002;200-201.
66. Bösmann, A.; Wasserscheid, P.; Bolm, C.; Keim, W. DE10003708 2001.
67. Kitazume, T. US 0031875 2001.
68. Levillain, J.; Dubant, G.; Abrunhosa, I.; Gulea, M.; Gaumont, A. C., submitted.
69. Baudoux, J.; Judeinstein, P.; Cahard, D.; Plaquevent, J. C., to be submitted.
70. Haramoto Y., Miyashita T., Nanasawa M., Aoki Y., Nohira H. Liq. Cryst. 29:2002;87-90.
71. Ishida Y., Miyauchi H., Saigo K. Chem. Commun. 2002;2240-2241.