Recent advances in iridium-catalyzed asymmetric hydrogenation: New catalysts, substrates and applications in total synthesis

Chimia

Volumn 66, Issue 4, 2012, Pages 187-191

  Ganić, Adnan ^a   Rageot, Denise ^a   Tröndlin, Lars ^a   Pfaltz, Andreas ^a  

^a UNIVERSITY OF BASEL   (Switzerland)

Author keywords

Asymmetric catalysis; Boron; Hydrogenation; Iridium; Natural products; P,O Ligands

Indexed keywords

EID: 84860711156     PISSN: 00094293     EISSN: None     Source Type: Journal    
DOI: 10.2533/chimia.2012.187     Document Type: Conference Paper

References (67)

1. G. Shang, W. Li, X. Zhang, in 'Catalytic Asymmetric Synthesis', 3rd ed., Ed. I. Ojima, Wiley, Hoboken, 2010, pp. 343.
2. a) W. S. Knowles, Angew. Chem. Int. Ed. 2002, 41, 1998;
3. b) R. Noyori, Angew. Chem. Int. Ed. 2002, 41, 2008.
4. a) L. A. Oro, D. Carmona, in 'Handbook of Homogeneous Hydrogenation', Vol. 1, Eds. J. G. de Vries, C. J. Elsevier, Wiley-VCH, Weinheim, 2007, pp. 3;
5. b) R. H. Morris, in 'Handbook of Homogeneous Hydrogenation', Vol. 1, Eds. J. G. de Vries, C. J. Elsevier, Wiley- VCH, Weinheim, 2007, pp. 45.
6. R. Crabtree, Acc. Chem. Res. 1979, 12, 331.
7. P. Schnider, G. Koch, R. Prétôt, G. Z. Wang, F. M. Bohnen, C. Krüger, A. Pfaltz, Chem. Eur. J. 1997, 3, 887.
8. A. Lightfoot, P. Schnider, A. Pfaltz, Angew. Chem. Int. Ed. 1998, 37, 2897.
9. I. Krossing, I. Raabe, Angew. Chem. Int. Ed. 2004, 43, 2066.
10. S. P. Smidt, N. Zimmermann, M. Studer, A. Pfaltz, Chem. Eur. J. 2004, 10, 4685.
11. a) D. H. Woodmansee, A. Pfaltz, Top. Organomet. Chem. 2011, 34, 31;
12. b) D. H. Woodmansee, A. Pfaltz, Chem. Commun. 2011, 47, 7912;
13. c) M. G. Schrems, A. Wang, A. Pfaltz, Chimia 2008, 62, 506;
14. d) S. J. Roseblade, A. Pfaltz, Acc. Chem. Res. 2007, 40, 1402;
15. e) S. Bell, B. Wüstenberg, S. Kaiser, F. Menges, T. Netscher, A. Pfaltz, Science 2006, 311, 642.
16. a) X. Li, Q. Li, X. Wu, Y. Gao, D. Xu, L. Kong, Tetrahedron: Asymm. 2007, 18, 629;
17. b) L. B. Schenkel, J. A. Ellman, J. Org. Chem. 2004, 69, 1800;
18. c) D. Liu, W. Tang, X. Zhang, Org. Lett. 2004, 6, 513;
19. d) P. G. Cozzi, F. Menges, S. Kaiser, Synlett 2003, 833;
20. e) T. Bunlaksananusorn, K. Polborn, P. Knochel, Angew. Chem. Int. Ed. 2003, 42, 3941.
21. a) J. Mazuela, P.-O. Norrby, P. G. Andersson, O. Pàmies, M. Diéguez, J. Am. Chem. Soc. 2011, 133, 13634;
22. b) O. Pàmies, P. G. Andersson, M. Diéguez, Chem. Eur. J. 2010, 16, 14232;
23. c) J. Mazuela, J. J. Verendel, M. Coll, B. Schaffner, A. Borner, P. G. Andersson, O. Pamies, M. Diéguez, J. Am. Chem. Soc. 2009, 131, 12344;
24. d) T. L. Church, P. G. Andersson, Coord. Chem. Rev. 2008, 252, 513;
25. e) K. Källström, I. Munslow, P. G. Andersson, Chem. Eur. J. 2006, 12, 3194.
26. a) X. Cui, K. Burgess, Chem. Rev. 2005, 105, 3272;
27. b) Y. Fan, X. Cui, K. Burgess, M. B. Hall, J. Am. Chem. Soc. 2004, 126, 16688.
28. M. Engman, J. S. Diesen, A. Paptchikhine, P. G. Andersson, J. Am. Chem. Soc. 2007, 129, 4536.
29. Y. Zhu, K. Burgess, Adv. Synth. Catal. 2008, 350, 979.
30. P. Cheruku, J. Diesen, P. G. Andersson, J. Am. Chem. Soc. 2008, 130, 5595.
31. P. Cheruku, A. Paptchikhine, T. L. Church, P. G. Andersson, J. Am. Chem. Soc. 2009, 131, 8285.
32. A. Paptchikhine, P. Cheruku, M. Engman, P. G. Andersson, Chem. Commun. 2009, 5996.
33. C. Valla, A. Baeza, F. Menges, A. Pfaltz, Synlett 2008, 3167.
34. S. Kaiser, S. R. Smidt, A. Pfaltz, Angew. Chem. Int. Ed. 2006, 45, 5194.
35. A. Baeza, A. Pfaltz, Chem. Eur. J. 2010, 16, 2036.
36. a) G.-H. Hou, J.-H. Xie, P.-C. Yan, Q.-L. Zhou, J. Am. Chem. Soc. 2009, 131, 1366;
37. b) A. Baeza, A. Pfaltz, Chem. Eur. J. 2009, 15, 2266.
38. a) A. Wang, B. Wüstenberg, A. Pfaltz, Angew. Chem. Int. Ed. 2008, 47, 2298;
39. b) J. Zhao, K. Burgess, J. Am. Chem. Soc. 2009, 131, 13236;
40. c) J. Zhou, K. Burgess, Angew. Chem. Int. Ed. 2007, 46, 1129.
41. a) S. Li, S.-F. Zhu, C.-M. Zhang, S. Song, Q.-L. Zhou, J. Am. Chem. Soc. 2008, 130, 8584;
42. b) S.- M. Lu, C. Bolm, Angew. Chem. Int. Ed. 2008, 47, 8920;
43. c) S.-M. Lu, C. Bolm, Chem. Eur. J. 2008, 14, 7513;
44. d) W.-J. Lu, Y.-W. Chen, X.-L. Hou, Angew. Chem. Int. Ed. 2008, 47, 10133;
45. e) W.-J. Lu, X.-L. Hou, Adv. Synth. Catal. 2009, 351, 1224.
46. D. Rageot, D. H. Woodmansee, B. Pugin, A. Pfaltz, Angew. Chem. Int. Ed. 2011, 50, 9598.
47. D. H. Woodmansee, M.-A. Müller, M. Neuburger, A. Pfaltz, Chem. Sci. 2010, 1, 72.
48. a) D. G. Hall, in 'Boronic Acids', Ed. D. G. Hall, Wiley-VCH, Weinheim, 2006, pp. 1;
49. b) H. C. Brown, B. Singaram, Acc. Chem. Res. 1988, 21, 287.
50. a) H. C. Brown, P. V. Ramachandran, Pure Appl. Chem. 1991, 63, 307;
51. b) H. C. Brown, P. V. Ramachandran, J. Organomet. Chem. 1995, 500, 1.
52. a) M. Ueda, A. Saitoh, N. Miyaura, J. Organomet. Chem. 2002, 642, 145;
53. b) W. J. Moran, J. P. Morken, Org. Lett. 2006, 8, 2413;
54. c) J. B. Morgan, J. P. Morken, J. Am. Chem. Soc. 2004, 126, 15338.
55. A. Ganić, A. Pfaltz, Chem. Eur. J. 2012, doi: 10.1002/chem. 201200246.
56. G. G. Bianco, H. M. C. Ferraz, A. M. Cost, L. V. Costa-Lotufo, C. Pessoa, M. O. de Moraes, M. G. Schrems, A. Pfaltz, L. F. Silva, J. Org. Chem. 2009, 74, 2561.
57. M. G. Schrems, A. Pfaltz, Chem. Commun. 2009, 6210.
58. T. Yoshinari, K. Ohmori, M. G. Schrems, A. Pfaltz, K. Suzuki, Angew. Chem. Int. Ed. 2010, 49, 881.
59. Y. Zhu, A. Loudet, K. Burgess, Org. Lett. 2010, 12, 4392.
60. a) H. J. Jessen, A. Schumacher, F. Schmid, A. Pfaltz, K. Gademann, Org. Lett. 2011, 13, 4368;
61. b) H. J. Jessen, A. Schumacher, T. Shaw, A. Pfaltz, K. Gademann, Angew. Chem. Int. Ed. 2011, 50, 4222.
62. D. Häbich, F. von Nussbaum, ChemMedChem 2006, 1, 951.
63. K. C. Nicolaou, A. Li, D. J. Edmonds, Angew. Chem. Int. Ed. 2006, 45, 7086.
64. For a recent review see: K. C. Nicolaou, J. S. Chen, D. J. Edmonds, A. A. Estrada, Angew. Chem. Int. Ed. 2009, 48, 660.
65. a) K. Tiefenbacher, J. Mulzer, Angew. Chem. Int. Ed. 2007, 46, 8074;
66. b) K. Tiefenbacher, J. Mulzer, Angew. Chem. Int. Ed. 2008, 47, 2548;
67. c) K. Tiefenbacher, L. Tröndlin, J. Mulzer, A. Pfaltz, Tetrahedron 2010, 66, 6508.