Enantioselective metal/organo-catalyzed aerobic oxidative sp3C-H olefination of tertiary amines using molecular oxygen as the sole oxidant

Journal of the American Chemical Society

Volumn 134, Issue 30, 2012, Pages 12334-12337

  Zhang, Gen ^a   Ma, Yunxia ^a   Wang, Shoulei ^a   Zhang, Yaohu ^a   Wang, Rui ^a  

^a LANZHOU UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ENANTIOSELECTIVE; ENVIRONMENTALLY-FRIENDLY; NOVEL STRATEGIES; OLEFINATION; OLEFINATION REACTION; OPTICALLY ACTIVE; ORGANOCATALYSIS; TERTIARY AMINE; TETRAHYDROISOQUINOLINES;

AMINES; OLEFINS; OXIDANTS;

CATALYSIS;

ALKENE; COPPER; OXYGEN; TERTIARY AMINE; TETRAHYDROISOQUINOLINE;

ANAEROBIC METABOLISM; ARTICLE; CATALYST; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; ENANTIOSELECTIVITY; OLEFINATION; STOICHIOMETRY;

ALKENES; AMINES; CATALYSIS; COPPER; ISOQUINOLINES; OXIDANTS; OXIDATION-REDUCTION; OXYGEN; STEREOISOMERISM;

EID: 84864469935     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja303333k     Document Type: Article

References (62)

1. Chen, X.; Engle, K. M.; Wang, D.-H.; Yu, J.-Q. Angew. Chem., Int. Ed. 2009, 48, 5094
2. Lyons, T. W.; Sanford, M. S. Chem. Rev. 2010, 110, 1147
3. Colby, D. A.; Bergman, R. G.; Ellman, J. A. Chem. Rev. 2010, 110, 624
4. Peng, H. M.; Dai, L.-X.; You, S.-L. Angew. Chem., Int. Ed. 2010, 49, 5826
5. Davies, H. M. L.; Bois, J. D.; Yu, J.-Q. Chem. Soc. Rev. 2011, 40, 1855
6. Zaitsev, V. G.; Daugulis, O. J. Am. Chem. Soc. 2005, 127, 4156
7. Cai, G.; Fu, Y.; Li, Y.; Wan, X.; Shi, Z. J. Am. Chem. Soc. 2007, 129, 7666
8. Zhang, Y.-H.; Shi, B.-F.; Yu, J.-Q. J. Am. Chem. Soc. 2009, 131, 5072
9. Wang, D.-H.; Engle, K. M.; Shi, B.-F.; Yu, J.-Q. Science 2010, 327, 315
10. Lu, Y.; Wang, D.-H.; Engle, K. M.; Yu, J.-Q. J. Am. Chem. Soc. 2010, 132, 5916
11. Ueura, K.; Satoh, T.; Miura, M. Org. Lett. 2007, 9, 1407
12. Umeda, N.; Hirano, K.; Satoh, T.; Miura, M. J. Org. Chem. 2009, 74, 7094
13. Patureau, F. W.; Glorius, F. J. Am. Chem. Soc. 2010, 132, 9992
14. Patureau, F. W.; Besset, T.; Glorius, F. Angew. Chem., Int. Ed. 2011, 50, 1064
15. Wasa, M.; Engle, K. M.; Yu, J.-Q. J. Am. Chem. Soc. 2010, 132, 3680
16. Stowers, K. J.; Fortner, K. C.; Sanford, M. S. J. Am. Chem. Soc. 2011, 133, 6541
17. Wasa, M.; Engle, K. M.; Lin, D. W.; Yoo, E. J.; Yu, J.-Q. J. Am. Chem. Soc. 2011, 133, 19598.
18. Shi, B.-F.; Zhang, Y.-H.; Lam, J. K.; Wang, D.-H.; Yu, J.-Q. J. Am. Chem. Soc. 2010, 132, 460
19. Shi, B.-F.; Maugel, N.; Zhang, Y.-H.; Yu, J.-Q. Angew. Chem., Int. Ed. 2008, 47, 4882
20. Bäckvall, J.-E. Modern Oxidation Methods, 2 nd ed.; Wiley-VCH: Weinheim, 2011.
21. Shi, W.; Liu, C.; Lei, A. Chem. Soc. Rev. 2011, 40, 2761
22. Caron, S.; Dugger, R. W.; Ruggeri, S. G.; Ragan, J. A.; Ripin, D. H. B. Chem. Rev. 2006, 106, 2943
23. Davies, H. M. L.; Manning, J. R. Nature 2008, 451, 417
24. Wendlandt, A. E.; Suess, A. M.; Stahl, S. S. Angew. Chem., Int. Ed. 2011, 50, 11062
25. Campos, K. R. Chem. Soc. Rev. 2007, 36, 1069
26. Murahashi, S.-I.; Zhang, D. Chem. Soc. Rev. 2008, 37, 1490
27. Li, C.-J. Acc. Chem. Res. 2009, 42, 335
28. Scheuermann, C. Chem. Asian J. 2010, 5, 436
29. Jones, K. M.; Klussmann, M. Synlett 2012, 23, 159
30. Sasamoto, N.; Dubs, C.; Hamashima, Y.; Sodeoka, M. J. Am. Chem. Soc. 2006, 128, 14010
31. Zhao, L.; Li, C.-J. Angew. Chem., Int. Ed. 2008, 47, 7075
32. Pintér, A.; Sud, A.; Sureshkumar, D.; Klussmann, M. Angew. Chem., Int. Ed. 2010, 49, 5004
33. Li, Z.; Li, C.-J. J. Am. Chem. Soc. 2005, 127, 3672
34. Murahashi, S.-I.; Nakae, T.; Terai, H.; Komiya, N. J. Am. Chem. Soc. 2008, 130, 11005
35. Allen, J. M.; Lambert, T. H. J. Am. Chem. Soc. 2011, 133, 1260
36. Li, Z.; Li, C.-J. J. Am. Chem. Soc. 2004, 126, 11810
37. Catino, A. J.; Nichols, J. M.; Nettles, B. J.; Doyle, M. P. J. Am. Chem. Soc. 2006, 128, 5648
38. Li, Z.; Bohle, D. S.; Li, C.-J. Proc. Natl. Acad. Sci. U.S.A. 2006, 103, 8928
39. Murahashi, S.-I.; Komiya, N.; Terai, H.; Nakae, T. J. Am. Chem. Soc. 2003, 125, 15312
40. Stahl, S. S. Angew. Chem., Int. Ed. 2004, 43, 3400
41. Punniyamurthy, T.; Velusamy, S.; Iqbal, J. Chem. Rev. 2005, 105, 2329
42. Gligorich, K. M.; Sigman, M. S. Chem. Commun. 2009, 3854
43. Shi, Z.; Zhang, C.; Tang, C.; Jiao, N. Chem. Soc. Rev. 2012, 41, 3381
44. Xia, X.-F.; Zhang, L.-L.; Song, X.-R.; Liu, X.-Y.; Liang, Y.-M. Org. Lett. 2012, 14, 2480
45. Zhang, G.; Zhang, Y.; Wang, R. Angew. Chem., Int. Ed. 2011, 50, 10429
46. Zhang, J.; Tiwari, B.; Xing, C.; Chen, X.; Chi, Y. R. Angew. Chem., Int. Ed. 2012, 51, 3649
47. Zhang, G.; Zhang, Y.; Jiang, X.; Yan, W.; Wang, R. Org. Lett. 2011, 13, 3806
48. Zhang, G.; Zhang, Y.; Yan, J.; Chen, R.; Wang, S.; Ma, Y.; Wang, R J. Org. Chem. 2012, 77, 878
49. Shao, Z.; Zhang, H. Chem. Soc. Rev. 2009, 38, 2745
50. Zhong, C.; Shi, X. Eur. J. Org. Chem. 2010, 2999
51. Jellerichs, B. G.; Kong, J.-R.; Krische, M. J. J. Am. Chem. Soc. 2003, 125, 7758
52. Ibrahem, I.; Córdova, A. Angew. Chem., Int. Ed. 2006, 45, 1952
53. Mukherjee, S.; List, B. J. Am. Chem. Soc. 2007, 129, 11336
54. Zhou, S.; Fleischer, S.; Junge, K.; Beller, M. Angew. Chem., Int. Ed. 2011, 50, 5120
55. Hu, W.; Xu, X.; Zhou, J.; Liu, W.-J.; Huang, H.; Hu, J.; Yang, L.; Gong, L.-Z. J. Am. Chem. Soc. 2008, 130, 7782
56. Webber, P.; Krische, M. J. J. Org. Chem. 2008, 73, 9379
57. Zhong, C.; Chen, Y.; Petersen, J. L.; Akhmedov, N.; Shi, X. Angew. Chem., Int. Ed. 2009, 48, 1279
58. Bandini, M.; Eichholzer, A.; Tragni, M.; Umani-Ronchi, A. Angew. Chem., Int. Ed. 2008, 47, 3238
59. He, R.; Shirakawa, S.; Maruoka, K. J. Am. Chem. Soc. 2009, 131, 16620
60. Chrzanowska, M.; Rozwadowska, M. D. Chem. Rev. 2004, 104, 3341
61. Bentley, K. W. Nat. Prod. Rep. 2004, 21, 395
62. CCDC874177 (3q) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/cgibin/catreq.cgi