Nonenzymatic kinetic resolution of amines in ionic liquids

Synlett

Volumn , Issue 2, 2008, Pages 268-272

  Sabot, Cyrille ^a   Subhash, Pithani V ^a   Valleix, Alain ^b   Arseniyadis, Stellios ^a   Mioskowski, Charles ^a,b  

^a CNRS   (France)

^b CEA SACLAY   (France)

Author keywords

Amines; Ionic liquids; Kinetic resolution; Nonenzymatic

Indexed keywords

AMINE; IONIC LIQUID;

ACETYLATION; ARTICLE; CHEMICAL STRUCTURE; ENANTIOSELECTIVITY; KINETICS; ROOM TEMPERATURE;

EID: 38849150987     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-1000879     Document Type: Article

References (44)

1. For recent reviews on ionic liquids, see: (a) Zhao, H.; Malhotra, S. V. Aldrichimica Acta 2002, 35, 75.
2. (b) Sheldon, R. Chem. Commun. 2001, 2399.
3. (c) Wasserscheid, P.; Kein, W. Angew. Chem. Int. Ed. 2001, 112, 3926.
4. (d) Welton, T. Chem. Rev. 1999, 99, 2071.
5. (e) Tzschucke, C. C.; Markert, C.; Bannwarth, W.; Roller, S.; Hebel, A.; Haag, R. Angew. Chem. Int. Ed. 2002, 41, 3964.
6. Yadav, J. S.; Reddy, B. V. S.; Basak, A. K.; Narsaiah, A. V. Tetrahedron 2004, 60, 2131.
7. (a) Anderson, K.; Fernández, S. C.; Hardacre, C.; Marr, P. C. Inorg. Chem. Commun. 2004, 7, 73.
8. (b) Berthod, M.; Joerger, J.-M.; Mignani, G.; Vaultier, M.; Lemaire, M. Tetrahedron: Asymmetry 2004, 15, 2219.
9. (c) Lee, S.-G.; Zhang, Y. J.; Piao, J. Y.; Yoon, H.; Song, C. E.; Choi, J. H.; Hong, J. Chem. Commun. 2003, 2624.
10. (d) Wolfson, A.; Vankelecom, I. F. J.; Jacobs, P. A. Tetrahedron Lett. 2003, 44, 1195.
11. (a) Itoh, T.; Han, S.; Matsushita, Y.; Hayase, S. Green Chem. 2004, 6, 437.
12. (b) Imrie, C.; Elago, E. R. T.; McCleland, C. W.; Williams, N. Chem. Commun. 2002, 159.
13. (a) Law, M. C.; Wong, K.-Y.; Chan, T. H. Green Chem. 2004, 6, 241.
14. (b) Yoo, K.; Namboodiri, V. V.; Varma, R. S.; Smirniotis, P. G. J. Catal. 2004, 222, 511.
15. (a) Baleizão, C.; Pires, N.; Gigante, B.; Curto, M. J. M. Tetrahedron Lett. 2004, 45, 4375.
16. (b) Gmouh, S.; Yang, H.; Vaultier, M. Org. Lett. 2003, 5, 2219.
17. (a) Zhao, G.; Jiang, T.; Gao, H.; Han, B.; Huang, J.; Sun, D. Green Chem. 2004, 6, 75.
18. (b) Kabalka, G. W.; Venkataiah, B.; Dong, G. Tetrahedron Lett. 2004, 45, 729.
19. (c) Yang, X.-F.; Wang, M.; Varma, R. S.; Li, C.-J. Org. Lett. 2003, 5, 657.
20. Bernini, R.; Coratti, A.; Fabrizi, G.; Goggiamani, A. Tetrahedron Lett. 2003, 44, 8991.
21. Smietana, M.; Mioskowski, C. Org. Lett. 2001, 3, 1037.
22. (a) Kumar, A.; Pawar, S. S. J. Org. Chem. 2004, 69, 1419.
23. (b) Yadav, J. S.; Reddy, B. V. S.; Reddy, J. S. S.; Rao, R. S. Tetrahedron 2003, 59, 1599.
24. (c) Meracz, I.; Oh, T. Tetrahedron Lett. 2003, 44, 6465.
25. (a) Wang, A.-E.; Zhong, J.; Xie, J.-H.; Li, K.; Zhou, Q.-L. Adv. Synth. Catal. 2004, 346, 595.
26. (b) Arentsen, K.; Caddick, S.; Cloke, F. G. N.; Herring, A. P.; Hitchcock, P. B. Tetrahedron Lett. 2004, 45, 3511.
27. (c) Jensen, J. F.; Johannsen, M. Org. Lett. 2003, 5, 3025.
28. (d) Miao, W.; Chan, T. H. Org. Lett. 2003, 5, 5003.
29. (e) Rajagopal, R.; Jarikote, D. V.; Srinivasan, K. V. Chem. Commun. 2002, 616.
30. (f) Park, S. B.; Alper, H. Org. Lett. 2003, 5, 3209.
31. (a) Erbeldinger, M.; Mesiano, A. J.; Russel, A. Biotechnol. Prog. 2000, 16, 1131.
32. (b) Lau, R. M.; Van Rantwijk, F.; Seddon, K. R.; Sheldon, R. A. Org. Lett. 2000, 2, 4189.
33. (c) Lundell, K.; Kurki, T.; Lindroos, M.; Kanerva, L. T. Adv. Synth. Catal. 2005, 347, 1110.
34. Kondo, K.; Kurosaki, T.; Murakami, Y. Synlett 1998, 725.
35. Ie, Y.; Fu, G. C. Chem. Commun. 2000, 119.
36. (a) Arai, S.; Bellemin-Laponnaz, S.; Fu, G. C. Angew. Chem. Int. Ed. 2001, 40, 234.
37. (b) Arp, F. O.; Fu, G. C. J. Am. Chem. Soc. 2006, 128, 14264.
38. Arseniyadis, S.; Valleix, A.; Wagner, A.; Mioskowski, C. Angew. Chem. Int. Ed. 2004, 43, 3314.
39. Arseniyadis, S.; Subhash, P. V.; Valleix, A.; Mathew, S. P.; Blackmond, D. G.; Wagner, A.; Mioskowski, C. J. Am. Chem. Soc. 2005, 127, 6138.
40. Arseniyadis, S.; Subhash, P. V.; Valleix, A.; Wagner, A.; Mioskowski, C. Chem. Commun. 2005, 3310.
41. Anstiss, M.; Nelson, A. Org. Biomol. Chem. 2006, 4, 4135.
42. 4 and evaporated under reduced pressure. The resulting residue was purified by flash chromatography on silica gel (EtOAc-hexane, 1:1), and the enantiomeric excess was determined by HPLC on a chiral stationary phase.
43. -, etc.) confers the basic character to the ionic liquids.
44. The equilibrium could be displaced in an enantioselective fashion by the acid-free sulfonamide.