Asymmetric catalysis with an inert chiral-at-metal iridium complex

Journal of the American Chemical Society

Volumn 135, Issue 29, 2013, Pages 10598-10601

  Chen, Liang An ^a   Xu, Weici ^a   Huang, Biao ^a   Ma, Jiajia ^a   Wang, Lun ^a   Xi, Jianwei ^a   Harms, Klaus ^b   Gong, Lei ^a   Meggers, Eric ^a,b  

^a XIAMEN UNIVERSITY   (China)

^b PHILIPPS UNIVERSITY MARBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ASYMMETRIC CATALYSIS; CATALYST LOADINGS; CATALYTIC ASYMMETRIC TRANSFER HYDROGENATIONS; COOPERATIVE INTERACTIONS; ENANTIOMERIC EXCESS; METAL COORDINATION; RIGID SCAFFOLDS; WEAK INTERACTIONS;

CATALYSIS; CATALYSTS; COORDINATION REACTIONS; FUNCTIONAL GROUPS; HYDROGEN BONDS; IRIDIUM; LOADING; METAL COMPLEXES;

IRIDIUM COMPOUNDS;

IRIDIUM COMPLEX; MOLECULAR SCAFFOLD;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; ENANTIOMER; HYDROGEN BOND;

ALKENES; CATALYSIS; COORDINATION COMPLEXES; HYDROGENATION; IRIDIUM; NITRO COMPOUNDS; STEREOISOMERISM;

EID: 84880764575     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja403777k     Document Type: Article

References (70)

1. Halpern, J.; Trost, B. M. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5347
2. Walsh, P. J.; Kozlowski, M. C. Fundamentals of Asymmetric Catalysis; University Science Books: Mill Valley, CA, 2009.
3. List, B.; Yang, J. W. Science 2006, 313, 1584
4. MacMillan, D. W. C. Nature 2008, 455, 304
5. Schreiner, P. R. Chem. Soc. Rev. 2003, 32, 289
6. Takemoto, Y. Org. Biomol. Chem. 2005, 3, 4299
7. Taylor, M. S.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2006, 45, 1520
8. Connon, S. J. Chem.-Eur. J. 2006, 12, 5418
9. Doyle, A. G.; Jacobsen, E. N. Chem. Rev. 2007, 107, 5713
10. Yu, X.; Wang, W. Chem.-Asian J. 2008, 3, 516
11. Zhang, Z.; Schreiner, P. R. Chem. Soc. Rev. 2009, 38, 1187
12. Knowles, R. R.; Jacobsen, E. N. Proc. Natl. Acad. Sci. U.S.A. 2010, 107, 20678
13. Loeb, S. J.; Mercer, D. J. Chem. Soc. Rev. 2010, 39, 3612
14. Reedijk, J. Chem. Soc. Rev. 2013, 42, 1776
15. Pierre, J.-L. Coord. Chem. Rev. 1998, 178-180, 1183
16. Knof, U.; von Zelewsky, A. Angew. Chem., Int. Ed. 1999, 38, 302
17. Brunner, H. Angew. Chem., Int. Ed. 1999, 38, 1194
18. Knight, P. D.; Scott, P. Coord. Chem. Rev. 2003, 242, 125
19. Ganter, C. Chem. Soc. Rev. 2003, 32, 130
20. Lacour, J.; Hebbe-Viton, V. Chem. Soc. Rev. 2003, 32, 373
21. Fontecave, M.; Hamelin, O.; Ménage, S. Top. Organomet. Chem. 2005, 15, 271
22. Meggers, E. Eur. J. Inorg. Chem. 2011, 2911
23. Bauer, E. B. Chem. Soc. Rev. 2012, 41, 3153
24. Crassous, J. Chem. Commun. 2012, 48, 9684
25. Constable, E. C. Chem. Soc. Rev. 2013, 42, 1427
26. Ganzmann, C.; Gladysz, J. A. Chem.-Eur. J. 2008, 14, 5397
27. Hamelin, O.; Rimboud, M.; Pécaut, J.; Fontecave, M. Inorg. Chem. 2007, 46, 5354
28. Chavarot, M.; Ménage, S.; Hamelin, O.; Charnay, F.; Pécaut, J.; Fontecave, M. Inorg. Chem. 2003, 42, 4810
29. Sato, I.; Kadowaki, K.; Ohgo, Y.; Soai, K.; Ogino, H. Chem. Commun. 2001, 1022
30. Brunner, H.; Wachter, J.; Schmidbauer, J.; Sheldrick, G. M.; Jones, P. G. Organometallics 1986, 5, 2212
31. Zwick, B. D.; Arif, A. M.; Patton, A. T.; Gladysz, J. A. Angew. Chem., Int. Ed. Engl. 1987, 26, 910
32. Kromm, K.; Zwick, B. D.; Meyer, O.; Hampel, F.; Gladysz, J. A. Chem.-Eur. J. 2001, 7, 2015
33. Kromm, K.; Osburn, P. L.; Gladysz, J. A. Organometallics 2002, 21, 4275
34. Seidel, F.; Gladysz, J. A. Synlett 2007, 986
35. Hayashi, T.; Kumada, M. Acc. Chem. Res. 1982, 15, 395
36. Togni, A.; Breutel, C.; Schnyder, A.; Spindler, F.; Landert, H.; Tijani, A. J. Am. Chem. Soc. 1994, 116, 4062
37. Kudis, S.; Helmchen, G. Angew. Chem., Int. Ed. 1998, 37, 3047
38. Ireland, T.; Grossheimann, G.; Wieser-Jeunesse, C.; Knochel, P. Angew. Chem., Int. Ed. 1999, 38, 3212
39. Fu, G. C. Acc. Chem. Res. 2000, 33, 412
40. Bolm, C.; Kesselgruber, M.; Hermanns, N.; Hildebrand, J. P.; Raabe, G. Angew. Chem., Int. Ed. 2001, 40, 1488
41. Gibson, S. E.; Ibrahim, H. Chem. Commun. 2002, 2465
42. Özçubukçu, S.; Schmidt, F.; Bolm, C. Org. Lett. 2005, 7, 1407
43. Fu, G. C. Acc. Chem. Res. 2006, 39, 853
44. Huang, H.; Peters, R. Angew. Chem., Int. Ed. 2009, 48, 604
45. Kanbayashi, N.; Onitsuka, K. J. Am. Chem. Soc. 2010, 132, 1206
46. Ogasawara, M.; Wu, W.-Y.; Arae, S.; Watanabe, S.; Morita, T.; Takahashi, T.; Kamikawa, K. Angew. Chem., Int. Ed. 2012, 51, 2951
47. Feng, L.; Geisselbrecht, Y.; Blanck, S.; Wilbuer, A.; Atilla-Gokcumen, G. E.; Filippakopoulos, P.; Kräling, K.; Celik, M. A.; Harms, K.; Maksimoska, J.; Marmorstein, R.; Frenking, G.; Knapp, S.; Essen, L.-O.; Meggers, E. J. Am. Chem. Soc. 2011, 133, 5976
48. Vachal, P.; Jacobsen, E. N. J. Am. Chem. Soc. 2002, 124, 10012
49. Wenzel, A. G.; Jacobsen, E. N. J. Am. Chem. Soc. 2002, 124, 12964
50. Okino, T.; Hoashi, Y.; Takemoto, Y. J. Am. Chem. Soc. 2003, 125, 12672
51. Herrera, R. P.; Sgarzani, V.; Bernardi, L.; Ricci, A. Angew. Chem., Int. Ed. 2005, 44, 6576
52. Sibi, M. P.; Itoh, K. J. Am. Chem. Soc. 2007, 129, 8064
53. Herrera, R. P.; Monge, D.; Martín-Zamora, E.; Fernández, R.; Lassaletta, J. M. Org. Lett. 2007, 9, 3303
54. You, S.-L. Chem.-Asian J. 2007, 2, 820
55. Yang, J. W.; Hechavarria Fonseca, M. T.; List, B. Angew. Chem., Int. Ed. 2004, 43, 6660
56. Zhang, Z. G.; Schreiner, P. R. Synthesis 2007, 2559
57. Martin, N. J. A.; Ozores, L.; List, B. J. Am. Chem. Soc. 2007, 129, 8976
58. Martin, N. J. A.; Cheng, X.; List, B. J. Am. Chem. Soc. 2008, 130, 13862
59. Schneider, J. F.; Lauber, M. B.; Muhr, V.; Kratzer, D.; Paradies, J. Org. Biomol. Chem. 2011, 9, 4323
60. Czekelius, C.; Carreira, E. M. Angew. Chem., Int. Ed. 2003, 42, 4293
61. Czekelius, C.; Carreira, E. M. Org. Lett. 2004, 6, 4575
62. Czekelius, C.; Carreira, E. M. Org. Process Res. Dev. 2007, 11, 633
63. Soltani, O.; Ariger, M. A.; Carreira, E. M. Org. Lett. 2009, 11, 4196
64. Tang, Y.; Xiang, J.; Cun, L.; Wang, Y.; Zhu, J.; Liao, J.; Deng, J. Tetrahedron: Asymmetry 2010, 21, 1900
65. Li, S.; Huang, K.; Cao, B.; Zhang, J.; Wu, W.; Zhang, X. Angew. Chem., Int. Ed. 2012, 51, 8573
66. Ohta, H.; Kobayashi, N.; Ozaki, K. J. Org. Chem. 1989, 54, 1802
67. Hall, M.; Stueckler, C.; Kroutil, W.; Macheroux, P.; Faber, K. Angew. Chem., Int. Ed. 2007, 46, 3934
68. Toogood, H. S.; Fryszkowska, A.; Hare, V.; Fisher, K.; Roujeinikova, A.; Leys, D.; Gardiner, J. M.; Stephens, G. M.; Scrutton, N. S. Adv. Synth. Catal. 2008, 350, 2789
69. Oberdorfer, G.; Gruber, K.; Faber, K.; Hall, M. Synlett 2012, 23, 1857
70. Giacalone, F.; Gruttadauria, M.; Agrigento, P.; Noto, R. Chem. Soc. Rev. 2012, 41, 2406