Iridium(iii)-bis(oxazolinyl)phenyl catalysts for enantioselective C-H functionalization

Chemical Science

Volumn 4, Issue 6, 2013, Pages 2590-2596

  Owens, Clayton P ^a   Varela álvarez, Adrián ^a   Boyarskikh, Vyacheslav ^a   Musaev, Djamaladdin G ^a   Davies, Huw M L ^a   Blakey, Simon B ^a  

^a EMORY UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

C-H FUNCTIONALIZATION; CATALYST LOADINGS; DENSITY FUNCTIONAL THEORY CALCULATIONS; ENANTIOSELECTIVE; IRIDIUM COMPLEX; REACTION YIELDS; STEREOCHEMICAL MODELS; TRIDENTATE LIGANDS;

CATALYSTS; DENSITY FUNCTIONAL THEORY; ENANTIOSELECTIVITY; IRIDIUM; IRIDIUM COMPOUNDS; NITROGEN COMPOUNDS;

LIGANDS;

EID: 84877770547     PISSN: 20416520     EISSN: 20416539     Source Type: Journal    
DOI: 10.1039/c3sc50886b     Document Type: Article

References (68)

1. J. Yamaguchi, A. D. Yamaguchi, K. Itami, Angew. Chem., Int. Ed., 2012, 51, 8960
2. W. R. Gutekunst, P. S. Baran, Chem. Soc. Rev., 2011, 40, 1976
3. T. Brückl, R. D. Baxter, Y. Ishihara, P. S. Baran, Acc. Chem. Res., 2011, 45, 826
4. L. McMurray, F. O'Hara, M. J. Gaunt, Chem. Soc. Rev., 2011, 40, 1885
5. J. F. Hartwig, Chem. Soc. Rev., 2011, 40, 1992
6. F. Collet, C. Lescot, P. Dauban, Chem. Soc. Rev., 2011, 40, 1926
7. H. M. L. Davies, D. Morton, Chem. Soc. Rev., 2011, 40, 1857
8. C.-M. Che, V. K.-Y. Lo, C.-Y. Zhou, J.-S. Huang, Chem. Soc. Rev., 2011, 40, 1950
9. H. Lu, X. P. Zhang, Chem. Soc. Rev., 2011, 40, 1899
10. T. W. Lyons, M. S. Sanford, Chem. Rev., 2010, 110, 1147
11. D. A. Colby, R. G. Bergman, J. A. Ellman, Chem. Rev., 2009, 110, 624
12. H. M. L. Davies and J. Hansen, in Catalytic Asymmetric Synthesis, ed. I. Ojima, Wiley, Hoboken, 3rd edn, 2010, ch. 4, pp. 163-226
13. K. Godula, D. Sames, Science, 2006, 312, 417
14. R. Giri, B.-F. Shi, K. M. Engle, N. Maugel, J.-Q. Yu, Chem. Soc. Rev., 2009, 38, 3242
15. A. R. Dick, M. S. Sanford, Tetrahedron, 2006, 62, 2439
16. H. M. L. Davies, J. R. Manning, Nature, 2008, 451, 417
17. M. P. Doyle, R. Duffy, M. Ratnikov, L. Zhou, Chem. Rev., 2010, 110, 704
18. H. M. L. Davies, R. E. J. Beckwith, Chem. Rev., 2003, 103, 2861
19. J. Du Bois, Org. Process Res. Dev., 2011, 15, 758
20. N. Boudét and S. B. Blakey, in Chiral Amine Synthesis: Methods, Developments, and Applications, ed. T. C. Nugent, Wiley-VCH, Weinheim, 2010, pp. 377-395
21. A. Gunay, K. H. Theopold, Chem. Rev., 2010, 110, 1060
22. M. Zhou, R. H. Crabtree, Chem. Soc. Rev., 2011, 40, 1875
23. J. Hansen, H. M. L. Davies, Coord. Chem. Rev., 2008, 252, 545
24. H. Suematsu, T. Katsuki, J. Am. Chem. Soc., 2009, 131, 14218
25. D. T. Boruta, O. Dmitrenko, G. P. Yap, J. M. Fox, Chem. Sci., 2012, 3, 1589
26. A. DeAngelis, O. Dmitrenko, J. M. Fox, J. Am. Chem. Soc., 2012, 134, 11035
27. A. DeAngelis, O. Dmitrenko, G. P. A. Yap, J. M. Fox, J. Am. Chem. Soc., 2009, 131, 7230
28. P. Panne, A. DeAngelis, J. M. Fox, Org. Lett., 2008, 10, 2987
29. P. Panne, J. M. Fox, J. Am. Chem. Soc., 2007, 129, 22
30. A. DeAngelis, V. W. Shurtleff, O. Dmitrenko, J. M. Fox, J. Am. Chem. Soc., 2011, 133, 1650
31. T. Goto, Y. Natori, K. Takeda, H. Nambu, S. Hashimoto, Tetrahedron: Asymmetry, 2011, 22, 907
32. A. DeAngelis, M. T. Taylor, J. M. Fox, J. Am. Chem. Soc., 2009, 131, 1101
33. A. DeAngelis, P. Panne, G. P. A. Yap, J. M. Fox, J. Org. Chem., 2008, 73, 1435
34. Y. Yasutomi, H. Suematsu, T. Katsuki, J. Am. Chem. Soc., 2010, 132, 4510
35. S. Kanchiku, H. Suematsu, K. Matsumoto, T. Uchida, T. Katsuki, Angew. Chem., Int. Ed., 2007, 46, 3889
36. H. Suematsu, S. Kanchiku, T. Uchida, T. Katsuki, J. Am. Chem. Soc., 2008, 130, 10327
37. M. Ichinose, H. Suematsu, T. Katsuki, Angew. Chem., Int. Ed., 2009, 48, 3121
38. M. Uehara, H. Suematsu, Y. Yasutomi, T. Katsuki, J. Am. Chem. Soc., 2011, 133, 170
39. M. Ichinose, H. Suematsu, Y. Yasutomi, Y. Nishioka, T. Uchida, T. Katsuki, Angew. Chem., Int. Ed., 2011, 50, 9884
40. K. Sun, R. Sachwani, K. J. Richert, T. G. Driver, Org. Lett., 2009, 11, 3598
41. I. K. Mangion, I. K. Nwamba, M. Shevlin, M. A. Huffman, Org. Lett., 2009, 11, 3566
42. I. K. Mangion, R. T. Ruck, N. Rivera, M. A. Huffman, M. Shevlin, Org. Lett., 2011, 13, 5480
43. J.-C. Wang, Z.-J. Xu, Z. Guo, Q.-H. Deng, C.-Y. Zhou, X.-L. Wan, C.-M. Che, Chem. Commun., 2012, 48, 4299
44. B. J. Anding, A. Ellern, L. K. Woo, Organometallics, 2012, 31, 3628
45. B. J. Anding, J. Brgoch, G. J. Miller, L. K. Woo, Organometallics, 2012, 31, 5586
46. E. Milczek, N. Boudét, S. B. Blakey, Angew. Chem., Int. Ed., 2008, 47, 6825
47. S. E. Denmark, R. A. Stavenger, A.-M. Faucher, J. P. Edwards, J. Org. Chem., 1997, 62, 3375
48. M. A. Stark, C. J. Richards, Tetrahedron Lett., 1997, 38, 5881
49. Y. Motoyama, N. Makihara, Y. Mikami, K. Aoki, H. Nishiyama, Chem. Lett., 1997, 951
50. J.-I. Ito, H. Nishiyama, Synlett, 2012, 509
51. J. L. Niu, X. Q. Hao, J. F. Gong, M. P. Song, Dalton Trans., 2011, 40, 5135
52. J.-I. Ito, H. Nishiyama, Top. Organomet. Chem., 2011, 37, 185
53. H. Nishiyama, J.-I. Ito, Chem. Commun., 2010, 46, 203
54. H. Nishiyama, Chem. Soc. Rev., 2007, 36, 1133
55. H. Nishiyama, J.-I. Ito, Chem. Commun., 2010, 46, 203
56. J. S. Fossey, C. J. Richards, Organometallics, 2004, 23, 367
57. J. M. Vila, M. Gayoso, M. T. Pereira, M. L. Torres, J. M. Fernández, A. Fernández, J. M. Ortiguiera, J. Organomet. Chem., 1996, 506, 165
58. J.-I. Ito, T. Shiomi, H. Nishiyama, Adv. Synth. Catal., 2006, 348, 1235
59. M. Gerisch, J. R. Krumper, R. G. Bergman, T. D. Tilley, J. Am. Chem. Soc., 2001, 123, 5818
60. S. H. Oakley, M. P. Coogan, R. J. Arthur, Organometallics, 2007, 26, 2285
61. J.-I. Ito, T. Kaneda, H. Nishiyama, Organometallics, 2012, 31, 4442
62. K. E. Allen, D. M. Heinekey, A. S. Goldman, K. I. Goldberg, Organometallics, 2013, 32, 1579
63. Y. Kanazawa, H. Nishiyama, Synlett, 2006, 3343
64. A. Bugarin, B. T. Connell, Organometallics, 2008, 27, 4357
65. H. M. L. Davies, D. G. Stafford, T. Hansen, Org. Lett., 1999, 10, 233
66. Y. Zhao, D. G. Truhlar, J. Chem. Phys., 2006, 125, 194101
67. H. Lebel, J.-F. Marcoux, C. Molinaro, A. B. Charette, Chem. Rev., 2003, 103, 977
68. G. Desimoni, G. Faita, P. Quadrelli, Chem. Rev., 2003, 103, 3119