Application of monodentate secondary phosphine oxides, a new class of chiral ligands, in Ir(I)-catalyzed asymmetric imine hydrogenation

Organic Letters

Volumn 5, Issue 9, 2003, Pages 1503-1506

  Jiang, Xiao Bin ^a   Minnaard, Adriaan J ^a   Hessen, Bart ^a   Feringa, Ben L ^a   Duchateau, Alexander L L ^b   Andrien, Jean G O ^b   Boogers, Jeroen A F ^b   De Vries, Johannes G ^a,b  

^a UNIVERSITY OF GRONINGEN   (Netherlands)

^b DSM RESEARCH   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

BROMINE DERIVATIVE; CHLORIDE; IMINE; IRIDIUM; LIGAND; MAGNESIUM DERIVATIVE; PHOSPHINE OXIDE DERIVATIVE; PYRIDINE;

ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHIRALITY; ENANTIOSELECTIVITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROGENATION; REDUCTION; SYNTHESIS;

EID: 0041808241     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol034282u     Document Type: Article

References (65)

1. Jacobsen, E. N.; Pfaltz, A.; Yamamoto H. Comprehensive Asymmetric Catalysis; Springer-Verlag: Berlin, 1999; Vols. 1-3.
2. (a) Ohkuma, T.; Kitamura, M.; Noyori, R. In Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; VCH Publishers, Inc.: New York, 2000; p 1.
3. (b) Laneman, S. A. In Handbook of Chiral Chemicals; Ager, D. J., Ed.; Marcel Dekker: New York, 1999; p 143.
4. (c) Brown, J. M. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H. Eds.; Springer: Berlin, 1999; Vol. 1, p 121.
5. (d) Börner, A.; Holz, J. In Transition Metals for Organic Synthesis. Building Blocks and Fine Chemicals; Beller, M., Bolm, C. Eds.; Wiley-VCH: Weinheim, Germany, 1998; Vol. 2, p 3.
6. (e) Burk, M. J.; Bienewald, F. In Transition Metals for Organic Synthesis. Building Blocks and Fine Chemicals; Beller, M., Bolm, C.; Wiley-VCH: Weinheim, Germany, 1998; Vol. 2, p 13.
7. (f) Nógrádi, M. Stereoselective Synthesis; VCH: Weinheim, Germany, 1987; p 53.
8. (g) Koenig, K. E. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: Orlando, 1985; Vol. 5, p 71.
9. Blaser, H.-U.; Spindler, F.; Studer, M. Appl. Catal., A 2001, 221, 119.
10. de Vries, J. G. In Encyclopedia of Catalysis; Horvath, I. T., Ed.; John Wiley & Sons: New York, 2003; Vol. 3, p 295. See also the on-line version: http://www.mrw.interscience.wiley.com/enccat/.
11. Feringa, B. L. Acc. Chem. Res. 2000, 33, 346.
12. (a) van den Berg, M.; Minnaard, A. J.; Schudde, E. P.; van Esch, J.; de Vries, A. H. M.; de Vries, J. G.; Feringa, B. L. J. Am. Chem. Soc. 2000, 122, 11539.
13. (b) van den Berg, M.; Minnaard, A. J.; de Vries, J. G.; Feringa, B. L. (DSM N. V.). WO 02/04466, 2002.
14. (c) van den Berg, M.; Minnaard, A. J.; Haak, R. M.; Leeman, M.; Schudde, E. P.; Meetsma, A.; Feringa, B. L.; de Vries, A. H. M.; Maljaars, C. E. P.; Willans, C. E.; Hyett, D.; Boogers, J. A. F.; Henderickx, H. J. W.; de Vries, J. G. Adv. Synth. Catal. 2003, 345, 308.
15. (d) Peña, D.; Minnaard, A. J.; de Vries, J. G.; Feringa, B. L. J. Am. Chem. Soc. 2002, 124, 14552.
16. (e) Zeng, Q.; Liu, H.; Mi, A.; Jiang, Y.; Li, X.; Choi, M. C. K.; Chan, A. S. C. Tetrahedron 2002, 58, 8799.
17. (a) van den Berg, M.; Haak, R. M.; Minnaard, A. J.; de Vries, A. H. M.; de Vries, J. G.; Feringa, B. L. Adv. Synth. Catal. 2002, 344, 1003.
18. (b) Jia, X.; Guo, R.; Li, X.; Yao, X.; Chan, A. S. C. Tetrahedron Lett. 2002, 43, 5541.
19. Claver, C.; Fernandez, E.; Gillon, A.; Heslop, K.; Hyett, D. J.; Martorell, A.; Orpen, A. G.; Pringle, P. G. Chem. Commun. 2000, 961.
20. Reetz, M. T.; Mehler, G. Angew. Chem., Int. Ed. 2000, 39, 3889.
21. (a) Guillen, F.; Fiaud, J.-C. Tetrahedron Lett. 1999, 40, 2939.
22. (b) Junge, K.; Oehme, G.; Monsees, A.; Riermeier, T.; Dingerdissen, U.; Beller, M. Tetrahedron Lett. 2002, 43, 4977.
23. (a) Spindler, F.; Blaser, H.-U. In Transition Metals for Organic Synthesis. Building Blocks and Fine Chemicals; Beller, M., Bolm, C., Eds.; Wiley-VCH: Weinheim, Germany, 1998; Vol. 2, p 69.
24. (b) Spindler, F.; Blaser, H.-U. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin, 1999; Vol. 1, p 248.
25. (a) Bakos, J.; Orosz, A.; Heil, B.; Laghmari, M.; Lhoste, P.; Sinou, D. J. Chem. Soc., Chem. Commun. 1991, 1684.
26. (b) Lensink, C.; de Vries, J. G. Tetrahedron: Asymmetry 1992, 3, 235.
27. (c) Lensink, C.; Rijnberg, E.; de Vries, J. G. J. Mol. Catal. A: Chem. 1997, 116, 199.
28. Willoughby, C. A.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 8952.
29. (a) Bader, R. R.; Baumeister, P.; Blaser, H.-U. Chimia 1996, 50, 99.
30. (b) Spindler, F.; Pugin, B.; Jalett, H.-P.; Buser, H.-P.; Pittelkow, U.; Blaser, H.-U. In Catalysis of Organic Reactions; Malz, R. E., Jr., Ed.; Marcel Dekker: New York, 1996; p 153.
31. (a) Uematsu, N.; Fujii, A.; Hashiguchi, S.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1996, 118, 4916.
32. (b) Sugi, K. D.; Nagata, T.; Yamada, T.; Mukaiyama, T. Chem. Lett. 1997, 493.
33. Kleiner, H.-J. In Houben-Weyl, Methoden der Organischen Chemie, 4 Auflage; Regitz, M., Ed.; Georg Thieme Verlag: Stuttgart, 1982; Band E1, p 240.
34. Gallagher, M.J. In The Chemistry of the Organophosphorus Compounds; Hartley, F.R., Ed.; John Wiley & Sons: Chichester, UK, 1992; Vol. 2, p 53.
35. Wang, F.; Polavarapu, P. L.; Drabowitz, J.; Mikolajczyk, M. J. Org. Chem. 2000, 65, 7561.
36. (a) Goerlich, J. R.; Fischer, A.; Jones, P. G.; Schmutzler, R., Z. Naturforsch., B: Chem. Sci. 1994, 49, 801.
37. (b) Heuer, L.; Jones, P. G.; Schmutzler, R. New J. Chem. 1990, 14, 891.
38. (c) Dixon, K. R.; Tattray, A. D.; Can. J. Chem. 1971, 49, 3997.
39. (a) Hoffmann, H.; Schellenbeck, P. Chem. Ber. 1966, 99, 1134.
40. (b) Farnham, W. B.; Lewis, R. A.; Murray, R. K.; Mislow, J. K. J. Am. Chem. Soc. 1970, 92, 5808.
41. (c) Horner, L.; Beck, P.; Toscano, V. G. Chem. Ber. 1961, 94, 1317.
42. Van Leeuwen, P. W. N. M.; Roobeek, C. F. In Homogeneous Transition Metal Catalalyzed Reactions. Advances in Chemistry Series 230; American Chemical Society: Washington, DC, 1992; p 367.
43. Ghaffar, T.; Parkins, A. W. Tetrahedron Lett. 1995, 36, 8657.
44. Cobley, C. J.; Heuvel, M. van den; Abbadi, A.; de Vries, J. G. Tetrahedron Lett. 2000, 41, 2467.
45. (a) Li, G. Y.; Zheng, G.; Noonan, A. F. J. Org. Chem. 2001, 66, 8677.
46. (b) Li, G. Y.; Fagan, P. J.; Watson, P. L. Angew. Chem., Int. Ed. 2001, 40, 1513-1516.
47. (c) Li, G. Y. (E. I. Du Pont de Nemours and Company, USA). U.S. Patent 6,124,462, 2000.
48. (d) Li, G. Y. (E. I. Du Pont de Nemours and Company, USA). U.S. Patent 6,291,722 B1, 2001.
49. Drabowicz, J.; Lyzwa, P.; Omelanczuk, J.; Pietrusiewicz, K. M.; Mikolayczyk, M. Tetrahedron: Asymmetry 1999, 10, 2757.
50. (a) Haynes, R. K.; Au-Yeung, T. L.; Chan, W. K.; Lam, W. L.; Li, Z. Y.; Yeung, L. L.; Chan, A. S. C.; Li, P.; Koen, M.; Mitchell, C. R.; Vonwiller, S. C. Eur. J. Org. Chem. 2000, 3205.
51. (b) Haynes, R. K.; Lam, W. W.; Yeung, L. L. Tetrahedron Lett. 1996, 37, 4729.
52. (c) Haynes, R. K.; Lam. W. W.; Williams, I. D.; Yeung, L. L. Chem. Eur. J. 1997, 3, 2052.
53. (d) Kawashima, T.; Iwanga, H.; Okazaki, R. Chem. Lett. 1993, 1531.
54. (e) Kawashima, T.; Iwanga, H.; Okazaki, R. Heteroatom Chem. 1995, 6, 235.
55. It has been suggested that protic solvents are a prerequisite for rhodium-catalyzed imine hydrogenation since the proton of the solvent bound to rhodium aids in shifting the imine from its n-bonded form to the π-bonded form that is required for its migratory insertion into the Rh-H bond. See: Longley, C.; Goodwin, T. J.; Wilkinson, G. Polyhedron 1986, 5, 1625.
56. Spindler, F.; Blaser, H. U. Adv. Synth. Catal. 2001, 343, 68.
57. (a) Vastag, S.; Bakos, J.; Toros, S.; Takach, N. E.; King, R. B.; Heil, B.; Marko, L. J. Mol. Catal. 1984, 22, 283.
58. (b) Spindler, F.; Pugin, B.; Blaser, H.-U. Angew. Chem., Int. Ed. Engl. 1990, 29, 558.
59. (c) Becalski, A. G.; Cullen, W. R.; Fryzuk, M. D.; James, B. R.; Kang, G. J.; Rettig, S. J. Inorg. Chem. 1991, 30, 5002.
60. Morimoto, T.; Nakajima, N.; Achiwa, K. Synlett 1995, 748.
61. Murata, S.; Sugimoto, T.; Matsuura, S. Heterocycles 1987, 26, 763.
62. Morimoto, T.; Suzuki, N.; Achiwa, K. Heterocycles 1996, 43, 2557.
63. Sablong, R.; Osborn, J. A. Tetrahedron Asymmetry 1996, 7, 3059.
64. Crabtree, R. H. Acc. Chem. Res. 1979, 12, 331.
65. Schnider, P.; Koch, G.; Prétôt, A.; Wang, G.; Bohnen, F. M. ; Kruger, C.; Pfaltz, A. Chem. Eur. J. 1997, 3, 887.