An efficient method for the synthesis of enantiopure phosphine-imidazoline ligands: Application to the Ir-catalyzed hydrogenation of imines

Tetrahedron Asymmetry

Volumn 15, Issue 21, 2004, Pages 3365-3373

  Guiu, Ester ^a   Claver, Carmen ^a   Benet Buchholz, Jordi ^b   Castillón, Sergio ^a  

^a UNIVERSITAT ROVIRA I VIRGILI   (Spain)

^b BAYER AG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ALKADIENE; IMIDAZOLINE DERIVATIVE; IMINE; IRIDIUM; NITROGEN; PHOSPHINE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL PROCEDURES; CHEMICAL REACTION; CHEMICAL STRUCTURE; ELECTRON; HYDROGENATION; PRIORITY JOURNAL; SYNTHESIS; X RAY DIFFRACTION;

EID: 7444223064     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetasy.2004.09.013     Document Type: Article

References (66)

1. Reviews about metal complexes with oxazoline ligands and their application: M. Gómez, G. Muller, and M. Rocamora Coord. Chem. Rev. 193 1999 769
2. A.K. Ghosh, P. Mathivanan, and J. Cappiello Tetrahedron: Asymmetry 9 1998 1
3. P.J. Guiry, and C.P. Saunders Adv. Synth. Catal. 346 2004 497
4. F. Menges, M. Neuburger, and A. Pfaltz Org. Lett. 4 2002 4713
5. A. Bastero, C. Claver, A. Ruiz, S. Castillón, E. Daura, C. Bo, and E. Zangrando Chem. Eur. J. 10 2004 3747
6. A. Bastero, A. Ruiz, C. Claver, and S. Castillón Eur. J. Inorg. 2001 3009
7. A.J. Davenport, D.L. Davies, J. Fawcett, and D.R. Russel J. Chem. Soc., Perkin Trans. 1 2001 1500
8. M. Casey, and M.P. Smyth Synlett 2003 102
9. C.A. Busacca, D. Grossbach, R.C. So, E.M. O'Brien, and E.M. Spinelli Org. Lett. 5 2003 595
10. Y.-R. Lin, X.-T. Zhou, L.-X. Dai, and J. Sun J. Org. Chem. 62 1997 1799
11. R.C.F. Jones, K.J. Howard, and J.S. Snaith Tetrahedron Lett. 37 1996 1707
12. T. Hayashi, E. Kishi, V.A. Soloshonok, and Y. Uozumi Tetrahedron Lett. 37 1996 4969
13. M.J. Hunter, and M.L. Ludwig J. Am. Chem. Soc. 91 1969 2429
14. N.W. Bristow J. Chem. Soc. 1957 513
15. K. Hartke, and A. Brutsche Synthesis 1992 1199
16. R. Baati, V. Gouverneur, and C. Mioskowski Synthesis 6 1999 927
17. A. Pinner, and F. Klein Ber. 10 1877 1889
18. W. Steinkopf, and W. Malinowski Ber. 44 1911 2898
19. B. Whelan, I. Iriepa, and E. Galvez Synthesis 1994 832
20. C. Dauwe, and J. Buddrus Synthesis 1995 171
21. T. Morimoto, K. Tachibana, and K. Achiwa Synlett 1997 783
22. G. Helmchen, S. Kudis, P. Sennhenn, and H. Steinhagen Pure Appl. Chem. 69 1997 513
23. N.A. Boland, M. Casey, S.J. Hynes, J.W. Mattews, and M.P. Smyth J. Org. Chem. 67 2002 3919
24. H. Takaya, T. Ohta, and R. Noyori I. Ojima Catal. Asymmetric Synth. 1993 John Wiley New York 31 Chapter 1
25. H.-U. Blaser, and F. Spindler E.N. Jacobsen A. Pfaltz H. Yamamoto Comprehensive Asymmetric Catalysis Vol. 1 1999 Springer Berlin 247 Chapter 6
26. Reviews of asymmetric hydrogenation of CC and CN: F. Spindler, and H.-U. Blaser M. Beller C. Bolm Transition Metals for Organic Synthesis Vol. 2 1998 J. Wiley & Sons Weinhem 69 Chapter 1
27. M.J. Palmer, and M. Wills Tetrahedron: Asymmetry 10 1999 2045
28. S. Kobayashi, and H. Ishitani Chem. Rev. 99 1999 1069
29. H.-U. Blaser, C. Malan, B. Pugin, F. Spindler, S. Heinz, and M. Studer Adv. Synth. Catal. 345 2003 103
30. R. Margalef-Català, P. Salagre, E. Fernández, and C. Claver Tetrahedron: Asymmetry 11 2000 1469
31. J.P. Cahill, A.P. Lightfoot, R. Goddard, J. Rust, and P.J. Guiry Tetrahedron: Asymmetry 9 1998 4307
32. I. Takei, Y. Nidhibayashi, Y. Arikawa, S. Uemura, and M. Hidai Organometallics 18 1999 2271
33. P.G. Cozzi, F. Menges, and S. Kaiser Synlett 6 2003 833
34. V. von Matt, and A. Pfaltz Angew. Chem., Int. Ed. Engl. 32 1993 566
35. P. Schnider, G. Koch, R. Prétot, W. Wang, F.M. Bohnen, C. Krüger, and A. Pfaltz Chem. Eur. J. 3 1997 887
36. S. Kainz, A. Brinkmann, W. Leitner, and A. Pfaltz J. Am. Chem. Soc. 121 1999 6421
37. A. Pfaltz Chimia 55 2001 708
38. E. Montenegro, R. Echarri, C. Claver, S. Castillón, A. Moyano, M.A. Pericàs, and A. Riera Tetrahedron: Asymmetry 7 1996 3553
39. F. Merchán, J. GarIÍn, V. Martínez, and E. Meléndez Synthesis 1982 482
40. G.J. Dawson, C.G. Frost, J.M.J. Williams, and S.J. Coote Tetrahedron Lett. 34 1993 3149
41. P. Cozzi, F. Menges, and S. Kaiser Synlett 6 2003 833
42. F. Menges, and A. Pfaltz Adv. Synth. Catal. 344 2002 40
43. I.C.M. Wehman-Ooyevaar, G.M. Kapteijn, D.M. Grove, W.J.J. Smeets, A.L. Spek, and G. van Koten J. Chem. Soc., Dalton Trans. 1994 652
44. A. Pfaltz, J. Blankestein, R. Hilgraf, E. Hörmann, S. McIntyre, F. Menges, M. Schönleber, S.P. Smidt, B. Wüstenberg, and N. Zimmermann Adv. Synth. Catal. 345 2003 33
45. H.P. Cahill, F.M. Bohnen, R. Goddard, C. Krügerand, and P. Guiry Tetrahedron: Asymmetry 9 1998 3831
46. H.D. Flack Acta Cryst. A39 1983 876
47. H.D. Flack, and G. Bernardinelli Acta Cryst. A55 1999 908
48. C. Bianchini, A. Meli, and F. Vizza Eur. J. Inorg. Chem. 2001 43
49. P. Barbaro, C. Bianchini, A. Meli, M. Moreno, and F. Vizza Organometallics 21 2002 1430
50. T. Morimoto, and K. Achiwa Tetrahedron: Asymmetry 6 1995 2661
51. T. Morimoto, N. Nakajima, and K. Achiwa Synlett 1995 748
52. R. Sablong, and J.A. Osborn Tetrahedron Lett. 37 1996 4937
53. S. Vastag, S. Bakos, S. Toros, N.E. Takach, R. King, B.B. Heil, and L. Marko J. Mol. Catal. 22 1984 283
54. G.-J. Kang, W.R. Cullen, M.D. Fryzuk, B.R. James, and J.P. Kutney J. Chem. Soc., Chem. Commun. 1988 1466
55. K. Tani, J. Onouchi, T. Yamagata, and Y. Kataoka Chem. Lett. 1995 955
56. K. Fagnou, and M. Lautens Angew. Chem., Int. Ed. 41 2002 26
57. G.-J. Kang, W.R. Cullen, M.D. Fryzuk, B.R. James, and J.P. Kutney J. Chem. Soc., Chem. Commun. 1988 1466
58. J. Bakos, I. Tóth, B. Heil, and L. Markó J. Organomet. Chem. 279 1985 23
59. F. Spindler, B. Pugin, and H.-U. Blaser Angew. Chem., Int. Ed. Engl. 29 1990 558
60. H.-U. Blazer, H.-P. Buser, K. Coers, R. Hanreich, H.-P. Jalett, E. Jelsch, B. Pugin, H.-D. Schneider, F. Spindler, and A. Wegmann Chimia 53 1999 275
61. Ng.C. Chan, and J.A. Osborn J. Am. Chem. Soc. 112 1990 9400
62. K. Inoguchi, S. Sakuraba, and K. Achiwa Synlett 1992 169
63. T.V. Rajan-Babu, T.A. Ayers, G.A. Halliday, K.K. You, and J.C. Calabrese J. Org. Chem. 62 1997 6012
64. D.S. Clyne, Y.C. Mermet-Bouvier, N. Nomura, and T.V. Rajanbabu J. Org. Chem. 64 1999 7601
65. A. Saitoh, K. Achiwa, K. Tanaka, and T. Morimoto J. Org. Chem. 65 2000 4228
66. V. Herrera, B. Muñoz, V. Landaeta, and N. Canudas J. Mol. Catal. 174 2001 141