Asymmetric addition of alkynes to imines in water catalyzed with a recyclable Cu(I)-bis(oxazoline) and stearic acid system

Tetrahedron Asymmetry

Volumn 18, Issue 3, 2007, Pages 396-399

  Liu, Juntao ^a   Liu, Bao ^a   Jia, Xian ^b   Li, Xingshu ^a   Chan, Albert S C ^a,c  

^a SUN YAT SEN UNIVERSITY   (China)

^b SHENYANG PHARMACEUTICAL UNIVERSITY   (China)

^c UNIVERSITY OF HONG KONG   (Hong Kong)

Author keywords

[No Author keywords available]

Indexed keywords

IMINE; OXAZOLINE DERIVATIVE; STEARIC ACID; WATER; ZINC DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; ENANTIOSELECTIVITY; PRIORITY JOURNAL;

EID: 33847617953     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2007.02.005     Document Type: Article

References (52)

1. Konishi M., Ohkuma H., Tsuno T., Oki T., VanDuyne G., and Clardy J. J. Am. Chem. Soc. 112 (1990) 3715
2. Huffman M.A., Yasuda N., DeCamp A.E., and Grabowski E.J. J. Org. Chem. 60 (1995) 1590
3. Nilsson B., Vargas H.M., Ringdahl B., and Hacksell U. J. Med. Chem. 35 (1992) 285
4. Miura M., Enna M., Okuro K., and Nomura M. J. Org. Chem. 60 (1995) 4999
5. Kauffman G.S., Harris G.D., Dorow R.L., Stone B.R.P., Parsons Jr. R.L., Pesti J.A., Magnus N.A., Fortunak J.M., Confalone P.N., and Nugent W.A. Org. Lett. 2 (2000) 3119
6. Huffman M.A., Yasuda N., DeCamp A.E., and Grabowski E.J.J. J. Org. Chem. 60 (1995) 1590
7. Enders D., and Reinhold U. Tetrahedron: Asymmetry 8 (1997) 1895
8. Lu G., Li Y.M., Li X.S., and Chan A.S.C. Coord. Chem. Rev. 249 (2005) 1736 and references cited therein
9. Takita R., Yakura K., Ohshima T., and Shibasaki M. J. Am. Chem. Soc. 127 (2005) 13760
10. Emmerson D.P.G., Hems W.P., and Davis B.G. Org. Lett. 8 (2006) 207
11. Wei C., and Li C.-J. J. Am. Chem. Soc. 124 (2002) 5638
12. Wei C., Mague J.T., and Li C.-J. Proc. Natl. Acad. Sci. U.S.A. 101 (2004) 5749
13. Traverse J.F., Hoveyda A.H., and Snapper M.L. Org. Lett. 5 (2003) 3273
14. Akullian L.C., Hoveyda A.H., and Snapper M.L. Angew. Chem., Int. Ed. 42 (2003) 4244
15. Koradin C., Polborn K., and Knochel P. Angew. Chem., Int. Ed. 41 (2002) 2535
16. Gommermann N., Koradin C., Polborn K., and Knochel P. Angew. Chem., Int. Ed. 42 (2003) 5763
17. Knopfel T.F., Aschwanden P., Ichikawa T., Watanabe T., and Carreira E.M. Angew. Chem., Int. Ed. 43 (2004) 5971
18. Rosa J.N., Santos A.G., and Afonso C.A.M. J. Mol. Catal. A: Chem. 214 (2004) 161
19. Rispens T., and Engberts J.B.F.N. Org. Lett. 3 (2001) 941
20. Otto S., Engberts J.B.F.N., and Kwak J.C.T. J. Am. Chem. Soc. 120 (1998) 9517
21. Peng Y.-Y., Ding Q.-P., Li Z., Wang P.G., and Cheng J.-P. Tetrahedron Lett. 44 (2003) 3871
22. Kobayashi S., and Manabe K. Acc. Chem. Res. 35 (2002) 209
23. Paetzold E., Oehme G., Fuhrmann H., Richter M., Eckelt R., Pohl M.-M., and Kosslick H. Micropor. Mesopor. Mater. 44-45 (2001) 517
24. Paetzold E., and Oehme G. J. Mol. Catal. A: Chem. 152 (2000) 69
25. Sinou D., Rabeyrin C., and Nguefack C. Adv. Synth. Catal. 345 (2003) 357
26. Cerichelli G., Cerritelli S., Chiarini M., De Maria P., and Fontana A. Chem.-Eur. J. 8 (2002) 5204
27. Kobayashi S., Lam W.W.-L., and Manabe K. Tetrahedron Lett. 41 (2000) 6115
28. Dwars T., and Oehme G. Adv. Synth. Catal. 344 (2002) 239
29. Grassert I., Kova'cs J., Fuhrmann H., and Oehme G. Adv. Synth. Catal. 344 (2002) 312
30. Fuhrmann H., Grassert I., Schareina T., Holzhüter G., and Oehme G. Macromol. Chem. Phys. 202 (2001) 426
31. Ludwig M., Kadyrov R., Fiedler H., Haage K., and Selke R. Chem.-Eur. J. 7 (2001) 3298
32. Robert F., Oehme G., Grassert I., and Sinou D. J. Mol. Catal. A: Chem. 156 (2000) 127
33. Oehme G., Grassert I., Paetzold E., Meisel R., Drexler K., and Fuhrmann H. Coord. Chem. Rev. 185-186 (1999) 585 and references cited therein
34. Grassert I., Schmidt U., Ziegler S., Fishcher C., and Oehme G. Tetrahedron: Asymmetry 9 (1998) 4193
35. Selke R., Holz J., Riepe A., and Börner A. Chem.-Eur. J. 4 (1998) 769
36. Schlatter A., Kundu M.K., and Woggon W.-D. Angew. Chem., Int. Ed. 43 (2004) 6731
37. Rhyoo H.Y., Park H.J., Suh W.H., and Chung Y.K. Tetrahedron Lett. 43 (2002) 269
38. Dioos B.M.L., Vankelecom I.F.J., and Jacobs P.A. Adv. Synth. Catal. 348 (2006) 1413 and references cited therein
39. Barbaro P. Chem.-Eur. J. 22 (2006) 5666 and references cited therein
40. Heitbaum M., Glorius F., and Escher I. Angew. Chem., Int. Ed. 45 (2006) 4732 and references cited therein
41. Matsuda T., Harada T., and Nakamura K. Curr. Org. Chem. 9 (2005) 299
42. Furno F., Licence P., Howdle S.M., and Poliakoff M. Actualite Chim. 4-5 (2003) 62
43. Wells S.L., and DeSimone J. Angew. Chem. Int. Ed. 40 (2001) 518
44. Baiker A. Chem. Rev. 99 (1999) 453
45. Jessop P.G., Ikariya T., and Noyori R. Chem. Rev. 99 (1999) 475
46. Yoshida J.-I., and Itami K. Chem. Rev. 102 (2002) 3693
47. Gladysz J.A., and Curran D.P. Tetrahedron 58 (2002) 3823
48. Curran D.P. Angew. Chem., Int. Ed. 37 (1998) 1175
49. Horváth I.T. Acc. Chem. Res. 31 (1998) 641
50. Handy S.T. Curr. Org. Chem. 9 (2005) 959
51. Handy S.T. Chem.-Eur. J. 9 (2003) 2938
52. Visser A.E., Swatloski R.P., Reichert W.M., Willauer H.D., Huddleston J.G., and Rogers R.D. NATO Sci. Ser. II: Math. Phys. Chem. 92 (2003) (Green Industrial Applications of Ionic Liquids)