Mixtures of chiral phosphorous acid diesters and achiral P ligands in the enantio- and diastereoselective hydrogenation of ketimines

Angewandte Chemie - International Edition

Volumn 46, Issue 24, 2007, Pages 4523-4526

  Reetz, Manfred T ^a   Bondarev, Oleg ^a  

^a MAX PLANCK INSTITUT FÜR KOHLENFORSCHUNG   (Germany)

Author keywords

Amines; Asymmetric catalysis; Combinatorial chemistry; Hydrogenation; Iridium

Indexed keywords

AMINES; CHIRALITY; ESTERS; HYDROGENATION; IRIDIUM; LIGANDS; STEREOSELECTIVITY;

ASYMMETRIC CATALYSIS; COMBINATORIAL CHEMISTRY; KETIMINES; PHOSPHITE;

PHOSPHORIC ACID;

EID: 34250782058     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200700533     Document Type: Article

References (71)

1. a) M. T. Reetz, G. Mehler, Angew. Chem. 2000, 112, 4047-4049;
2. Angew. Chem. Int. Ed. 2000, 39, 3889-3890;
3. b) M. T. Reetz, G. Mehler, A. Meiswinkel (SGK), patent application DE-A 10027505.2, June 6, 2000.
4. a) C. Claver, E. Fernandez, A. Gillon, K. Heslop, D. J. Hyett, A. Martorell, A. G. Orpen, P. G. Pringle, Chem. Commun. 2000, 961-962;
5. b) M. T. Reetz, T. Sell, Tetrahedron Lett. 2000, 41, 6333-6336.
6. a) M. van den Berg, A. J. Minnaard, E. P. Schudde, J. van Esch, A. H. M. de Vries, J. G. de Vries, B. L. Feringa, J. Am. Chem. Soc. 2000, 122, 11 539-11 540;
7. b) M. van den Berg, A. J. Minnaard, A. Jacobus, B. Feringa, J. G. de Vries (DSM NV), patent application NL 1015655C, July 7, 2000.
8. a) M. T. Reetz in Comprehensive Coordination Chemistry II, Vol. 9 (Ed.: M. D. Ward), Elsevier, Amsterdam, 2004, pp. 509-548;
9. b) H. Bernsmann, M. van den Berg, R. Hoen, A. J. Minnaard, G. Mehler, M. T. Reetz, J. G. de Vries, B. L. Feringa, J. Org. Chem. 2005, 70, 943-951.
10. Reviews of monodentate P ligands: a) F. Lagasse, H. B. Kagan, Chem. Pharm. Bull. 2000, 48, 315-324;
11. b) I. V. Komarov, A. Börner, Angew. Chem. 2001, 113, 1237-1240;
12. Angew. Chem. Int. Ed. 2001, 40, 1197-1200;
13. c) T. Jerphagnon, J.-L. Renaud, C. Bruneau, Tetrahedron: Asymmetry 2004, 15, 2101-2111;
14. d) J. Ansell, M. Wills, Chem. Soc. Rev. 2002, 31, 259-268;
15. e) B. D. Chapsal, Z. Hua, I. Ojima, Tetrahedron: Asymmetry 2006, 17, 642-657.
16. a) M. T. Reetz, A. Meiswinkel, G. Mehler, K. Angermund, M. Graf, W. Thiel, R. Mynott, D. G. Blackmond, J. Am. Chem. Soc. 2005, 127, 10 305-10 313;
17. b) I. D. Gridnev, C. Fan, P. G. Pringle, Chem. Commun. 2007, 1319-1321.
18. a) M. T. Reetz, T. Sell, A. Meiswinkel, G. Mehler, Angew. Chem. 2003, 115, 814-817;
19. Angew. Chem. Int. Ed. 2003, 42, 790-793;
20. b) M. T. Reetz, T. Sell, A. Meiswinkel, G. Mehler (SGK), patent application DE-A 10247633A1, October 11, 2002.
21. a) M. T. Reetz, Chim. Oggi 2003, 21(10/11), 5-8;
22. b) M. T. Reetz, X. Li, Tetrahedron 2004, 60, 9709-9714;
23. c) M. T. Reetz, G. Mehler, A. Meiswinkel, T. Sell, Tetrahedron: Asymmetry 2004, 15, 2165-2167;
24. d) M. T. Reetz, H. Guo, Beilstein J. Org. Chem. 2005, 1, 3;
25. e) M. T. Reetz, Y. Fu, A. Meiswinkel, Angew. Chem. 2006, 118, 1440-1443;
26. Angew. Chem. Int. Ed. 2006, 45, 1412-1415;
27. f) M. T. Reetz, M. Surowiec, Heterocycles 2006, 67, 567-574.
28. a) M. T. Reetz, G. Mehler, Tetrahedron Lett. 2003, 44, 4593-4596;
29. b) M. T. Reetz, X. Li, Angew. Chem. 2005, 117, 3019-3021;
30. Angew. Chem. Int. Ed. 2005, 44, 2959-2962;
31. c) M. T. Reetz, X. Li, Angew. Chem. 2005, 117, 3022-3024;
32. Angew. Chem. Int. Ed. 2005, 44, 2962-2964.
33. a) D. Peña, A. J. Minnaard, J. A. F. Boogers, A. H. M. de Vries, J. G. de Vries, B. L. Feringa, Org. Biomol. Chem. 2003, 1, 1087-1089;
34. b) R. Hoen, J. A. F. Boogers, H. Bernsmann, A. J. Minnaard, A. Meetsma, T. D. Tiemersma-Wegman, A. H. M. de Vries, J. G. de Vries, B. L. Feringa, Angew. Chem. 2005, 117, 4281-4284;
35. Angew. Chem. Int. Ed. 2005, 44, 4209-4212;
36. c) A. Duursma, D. Peña, A. J. Minnaard, B. L. Feringa, Tetrahedron: Asymmetry 2005, 16, 1901-1904;
37. d) C. Monti, C. Gennari, U. Piarulli, Tetrahedron Lett. 2004, 45, 6859-6862;
38. e) C. Monti, C. Gennari, U. Piarulli, J. G. de Vries, A. H. M. de Vries, L. Lefort, Chem. Eur. J. 2005, 11, 6701-6717.
39. Screening methods: a) M. T. Reetz, Angew. Chem. 2001, 113, 292-320;
40. Angew. Chem. Int. Ed. 2001, 40, 284-310;
41. b) M. T. Reetz, Angew. Chem. 2002, 114, 1391-1394;
42. Angew. Chem. Int. Ed. 2002, 41, 1335-1338;
43. c) K. Ding, H. Du, Y. Yuan, J. Long, Chem. Eur. J. 2004, 10, 2872-2884;
44. d) L. Lefort, A. F. Boogers, A. H. M. de Vries, J. G. de Vries, Org. Lett. 2004, 6, 1733-1735;
45. e) C. Jäkel, R. Paciello, Chem. Rev. 2006, 106, 2912-2942.
46. a) M. T. Reetz, T. Sell, R. Goddard, Chimia 2003, 57, 290-292;
47. For the taddol ((R,R)-4,5-bis(diphenylhydroxymethyl)-2,2-dimethyl- 1,3-dioxolane) analogue of 4, see: b) D. Enders, L. Tedeschi, J. W. Bats, Angew. Chem. 2000, 112, 4774-4776;
48. Angew. Chem. Int. Ed. 2000, 39, 4605-4607;
49. c) A. Alexakis, J. Burton, J. Vastra, C. Benhaim, X. Fournioux, A. van den Heuvel, J.-M. Levêque, F. Mazé, S. Rosset, Eur. J. Org. Chem. 2000, 4011-4027;
50. d) X. Jiang, A. J. Minnaard, B. Hessen, B. L. Feringa, A. L. L. Duchateau, J. G. O. Andrien, J. A. F. Boogers, J. G. de Vries, Org. Lett. 2003, 5, 1503-1506.
51. a) L. D. Quin, A Guide to Organophosphorus Chemistry, Wiley-Interscience, New York, 2000;
52. b) B. Walther, Coord. Chem. Rev. 1984, 60, 67-105;
53. c) N. V. Dubrovina, A. Börner, Angew. Chem. 2004, 116, 6007-6010;
54. Angew. Chem. Int. Ed. 2004, 43, 5883-5886;
55. d) L. Ackermann, Synlett 2007, 507-526.
56. Recent examples of asymmetric transition-metal-catalyzed ketimine hydrogenation (and literature cited therein): a) E. Guiu, M. Aghmiz, Y. Díaz, C. Claver, B. Meseguer, C. Militzer, S. Castillón, Eur. J. Org. Chem. 2006, 627-633;
57. b) T. Imamoto, N. Iwadate, K. Yoshida, Org. Lett. 2006, 8, 2289-2292;
58. c) A. Dervisi, C. Carcedo, L. Ooi, Adv. Synth. Catal. 2006, 348, 175-183;
59. d) G. Shang, Q. Yang, X. Zhang, Angew. Chem. 2006, 118, 6508-6510;
60. Angew. Chem. Int. Ed. 2006, 45, 6360-6362;
61. e) C. Moessner, C. Bolm, Angew. Chem. 2005, 117, 7736-7739;
62. Angew. Chem. Int. Ed. 2005, 44, 7564-7567;
63. f) A. Trifonova, J. S. Diesen, C. J. Chapman, P. G. Andersson, Org. Lett. 2004, 6, 3825-3827;
64. g) M. Solinas, A. Pfaltz, P. G. Cozzi, W. Leitner, J. Am. Chem. Soc. 2004, 126, 16 142-16 147;
65. h) D. Xiao, X. Zhang, Angew. Chem. 2001, 113, 3533-3536;
66. Angew. Chem. Int. Ed. 2001, 40, 3425-3428.
67. a) Review of substrate-directable diastereoselective reactions of chiral compounds: A. H. Hoveyda, D. A. Evans, G. C. Fu, Chem. Rev. 1993, 93, 1307-1370;
68. b) Synthesis and reactions of 12: C. Lensink, J. G. de Vries, Tetrahedron: Asymmetry 1993, 4, 215-222.
69. a) A. Horeau, H. B. Kagan, J. P. Vigneron, Bull. Soc. Chim. Fr. 1968, 9, 3795-3797;
70. b) S. Masamune, W. Choy, J. S. Petersen, L. R. Sita, Angew. Chem. 1985, 97, 1-31;
71. Angew. Chem. Int. Ed. Engl. 1985, 24, 1-30.