Catalytic asymmetric activation of a Csp3-H bond adjacent to a nitrogen atom: A versatile approach to optically active α-alkyl α-amino acids and C1-alkylated tetrahydroisoquinoline derivatives

Angewandte Chemie - International Edition

Volumn 50, Issue 44, 2011, Pages 10429-10432

  Zhang, Gen ^a   Zhang, Yaohu ^a   Wang, Rui ^a,b  

^a LANZHOU UNIVERSITY   (China)

^b HONG KONG POLYTECHNIC UNIVERSITY   (Hong Kong)

Author keywords

2,3 dichloro 5,6 dicyanoquinone; amino acids; asymmetric synthesis; C H activation; homogeneous catalysis

Indexed keywords

2,3-DICHLORO-5,6- DICYANOQUINONE; ASYMMETRIC ACTIVATION; ASYMMETRIC SYNTHESIS; C-H ACTIVATION; ENANTIOSELECTIVE ALKYLATION; ENVIRONMENTALLY-FRIENDLY; H-BONDS; HOMOGENEOUS CATALYSIS; NITROGEN ATOM; NOVEL STRATEGIES; ONE POT; OPTICALLY ACTIVE; TETRAHYDROISOQUINOLINES;

ACTIVATION ANALYSIS; AROMATIC COMPOUNDS; REACTION KINETICS;

AMINO ACIDS;

AMINO ACID; CARBON; CHLORINE; HYDROGEN; NITROGEN; TETRAHYDROISOQUINOLINE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMISTRY; SYNTHESIS;

AMINO ACIDS; CARBON; CATALYSIS; CHLORINE; HYDROGEN; NITROGEN; TETRAHYDROISOQUINOLINES;

EID: 80054982157     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201105123     Document Type: Article

References (70)

1. For recent reviews of C-H activation, see: "C-H Activation": Topics in Current Chemistry (Eds.:, J. Q. Yu, Z. Shi,), Springer, Berlin, 2010
2. K. Godula, D. Sames, Science 2006, 312, 67
3. R. G. Bergman, Nature 2007, 446, 391
4. K. R. Campos, Chem. Soc. Rev. 2007, 36, 1069
5. J. C. Lewis, R. G. Bergman, J. A. Ellman, Acc. Chem. Res. 2008, 41, 1013
6. X. Chen, K. M. Engle, D.-H. Wang, J.-Q. Yu, Angew. Chem. 2009, 121, 5196
7. Angew. Chem. Int. Ed. 2009, 48, 5094
8. S.-I. Murahashi, D. Zhang, Chem. Soc. Rev. 2008, 37, 1490.
9. H. M. L. Davies, Angew. Chem. 2006, 118, 6574
10. Angew. Chem. Int. Ed. 2006, 45, 6422
11. H. M. L. Davies, R. E. J. Beckwith, Chem. Rev. 2003, 103, 2861
12. H. M. L. Davies, J. R. Manning, Nature 2008, 451, 417
13. P. Müller, C. Fruit, Chem. Rev. 2003, 103, 2905.
14. For reviews on CDC reactions, see: C.-J. Li, Z. Li, Pure Appl. Chem. 2006, 78, 935
15. C.-J. Li, Acc. Chem. Res. 2009, 42, 335
16. C. Scheuermann, Chem. Asian J. 2010, 5, 436.
17. For CDC reactions of benzylic C-H bonds, see: Z. Li, L. Cao, C.-J. Li, Angew. Chem. 2007, 119, 6625
18. Angew. Chem. Int. Ed. 2007, 46, 6505
19. F. Benfatti, M. G. Capdevila, L. Zoli, E. Benedetto, G. Cozzi, Chem. Commun. 2009, 5919
20. A. Pintér, A. Sud, D. Sureshkumar, M. Klussmann, Angew. Chem. 2010, 122, 5124
21. Angew. Chem. Int. Ed. 2010, 49, 5004
22. D. J. Covell, M. C. White, Angew. Chem. 2008, 120, 6548
23. Angew. Chem. Int. Ed. 2008, 47, 6448
24. T. D. Beeson, A. Mastracchio, J. B. Hong, K. Ashton, D. W. Macmillan, Science 2007, 316, 582.
25. For CDC reactions of α-C-H bonds of second and tertiary amines, see: Z. Li, C.-J. Li, J. Am. Chem. Soc. 2004, 126, 11810
26. Z. Li, P. D. MacLeod, C.-J. Li, Tetrahedron: Asymmetry 2006, 17, 590
27. Z. Li, C.-J. Li, Org. Lett. 2004, 6, 4997
28. O. Baslé, C.-J. Li, Org. Lett. 2008, 10, 3661
29. I. Ibrahem, J. S. M. Samec, J. E. Bäckvall, A. Cõrdova, Tetrahedron Lett. 2005, 46, 3965
30. N. Sasamoto, C. Dubs, Y. Hamashima, M. Sodeoka, J. Am. Chem. Soc. 2006, 128, 14010
31. S.-I. Murahashi, T. Nakae, H. Terai, N. Komiya, J. Am. Chem. Soc. 2008, 130, 11005.
32. K. Maruoka, T. Ooi, Chem. Rev. 2003, 103, 3013
33. P. Beak, W. J. Zajdel, D. B. Reitz, Chem. Rev. 1984, 84, 471.
34. L. Zhao, C.-J. Li, Angew. Chem. 2008, 120, 7183
35. Angew. Chem. Int. Ed. 2008, 47, 7075
36. L. Zhao, O. Basle, C.-J. Li, Proc. Natl. Acad. Sci. USA 2009, 106, 4106
37. S.-I. Murahashi, A. Mitani, K. Kitao, Tetrahedron Lett. 2000, 41, 10245.
38. J. Xie, Z.-Z. Huang, Angew. Chem. 2010, 122, 10379
39. Angew. Chem. Int. Ed. 2010, 49, 10181.
40. H. Wang, R. Wang, H. Nie, R. Zhang, J.-T. Qiao, Peptides 2000, 89, 7
41. H.-M. Liu, X.-F. Liu, J.-L. Yao, C.-L. Wang, Y. Yu, R. Wang, J. Pharmacol. Exp. Ther. 2006, 319, 308.
42. S. Suga, S. Suzuki, J. Yoshida, J. Am. Chem. Soc. 2002, 124, 30
43. S.-I. Murahashi, T. Naota, H. Taki, J. Chem. Soc. Chem. Commun. 1985, 613
44. A. H. Éll, J. S. M. Samec, C. Brasse, J.-E. Bäckvall, Chem. Commun. 2002, 1144
45. S.-I. Murahashi, Y. Okano, H. Sato, T. Nakae, N. Komiya, Synlett 2007, 1675.
46. K. Juhl, N. Gathergood, K. A. Jørgensen, Angew. Chem. 2003, 115, 1536
47. Angew. Chem. Int. Ed. 2003, 42, 1498
48. D. A. Evans, D. Seidel, J. Am. Chem. Soc. 2005, 127, 9958
49. M. Agostinho, S. Kobayashi, J. Am. Chem. Soc. 2008, 130, 2430
50. T. Tsubogo, Y. Yamashita, S. Kobayashi, Angew. Chem. 2009, 121, 9281
51. Angew. Chem. Int. Ed. 2009, 48, 9117
52. M. Hatano, T. Horibe, K. Ishihara, J. Am. Chem. Soc. 2010, 132, 56.
53. W. Tu, P. E. Floreancig, Angew. Chem. 2009, 121, 4637
54. Angew. Chem. Int. Ed. 2009, 48, 4567
55. L. Liu, P. E. Floreancig, Angew. Chem. 2010, 122, 6030
56. Angew. Chem. Int. Ed. 2010, 49, 5894
57. C. Guo, J. Song, S. W. Luo, L.-Z. Gong, Angew. Chem. 2010, 122, 5690
58. Angew. Chem. Int. Ed. 2010, 49, 5558
59. Y. Hayashi, T. Itoh, H. Ishikawa, Angew. Chem. 2011, 123, 4006
60. Angew. Chem. Int. Ed. 2011, 50, 3920
61. S.-L. Zhang, H.-X. Xie, J. Zhu, H. Li, X.-S. Zhang, J. Li, W. Wang, Nat. Commun. 2011, 2, 211.
62. M. Chrzanowska, M. D. Rozwadowska, Chem. Rev. 2004, 104, 3341
63. K. W. Bentley, Nat. Prod. Rep. 2004, 21, 395.
64. D. Zhao, Y. Yuan, A. S. C. Chan, R. Wang, Chem. Eur. J. 2009, 15, 2738
65. L. Hong, W. Sun, C. Liu, D. Zhao, R. Wang, Chem. Commun. 2010, 46, 2856.
66. W. S. Wadsworth, W. D. Emmons, J. Am. Chem. Soc. 1961, 83, 1733
67. B. E. Maryanoff, A. B. Reize, Chem. Rev. 1989, 89, 863.
68. N. J. Leonard, G. W. Leubner, J. Am. Chem. Soc. 1949, 71, 3408
69. S.-I. Murahashi, N. Komiya, H. Terai, Angew. Chem. 2005, 117, 7091
70. Angew. Chem. Int. Ed. 2005, 44, 6931.