Dehydrogenative cross-coupling reaction by cooperative transition-metal and Brønsted acid catalysis for the synthesis of β-quinolinyl α-amino acid esters

Organic Letters

Volumn 16, Issue 18, 2014, Pages 4881-4883

  Zhu, Zhi Qiang ^a   Bai, Peng ^a   Huang, Zhi Zhen ^a,b  

^a ZHEJIANG UNIVERSITY   (China)

^b NANKAI UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID; COPPER; ESTER; GLYCINE; QUINOLINE DERIVATIVE; TRANSITION ELEMENT;

CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; METABOLISM; STEREOISOMERISM; SYNTHESIS;

AMINO ACIDS; CATALYSIS; COPPER; ESTERS; GLYCINE; MOLECULAR STRUCTURE; QUINOLINES; STEREOISOMERISM; TRANSITION ELEMENTS;

EID: 84908423258     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol502402s     Document Type: Article

References (53)

1. For selected reviews on DCC reactions: (a) Li, C.-J.; Li, Z. Pure Appl. Chem. 2006, 78, 935.
2. (b) Li, C.-J. Acc. Chem. Res. 2009, 42, 335-344.
3. (c) Scheuermann, C. Chem.-Asian J. 2010, 5, 436.
4. (d) Ashenhurst, J. A. Chem. Soc. Rev. 2010, 39, 540.
5. (e) Cho, S. H.; Kim, J. Y.; Kwak, J.; Chang, S. Chem. Soc. Rev. 2011, 40, 5068.
6. (f) Le Bras, J.; Muzart, J. Chem. Rev. 2011, 111, 1170.
7. (g) Yeung, C. S.; Dong, V. M. Chem. Rev. 2011, 111, 1215.
8. (h) Liu, C; Zhang, H.; Shi, W.; Lei, A. Chem. Rev. 2011, 111, 1780.
9. (i) Zhang, C; Tang, C; Jiao, N. Chem. Soc. Rev. 2012, 41, 3464.
10. (j) Girard, S. A.; Knauber, T.; Li, C.-J. Angew. Chem., Int. Ed. 2014, 53, 74.
11. For DCC reactions of α-amino acid derivatives: (a) Zhao, L.; Li, C.-J. Angew. Chem. 2008, 120, 7183;
12. Angew. Chem., Int. Ed. 2008, 47, 7075.
13. (b) Xie, J.; Huang, Z.-Z. Angew. Chem. 2010, 122, 10379;
14. Angew. Chem., Int. Ed. 2010, 49, 10181.
15. (c) Zhag, G.; Zhang, Y.; Wang, R. Angew. Chem. 2011, 123, 10613;
16. Angew. Chem., Int. Ed. 2011, 50, 10429.
17. (d) Zhu, S. Q.; Rueping, M. Chem. Commun. 2012, 48, 11960.
18. (e) Liu, P.; Wang, Z.; Lin, J.; Hu, X. Eur. J. Org. Chem. 2012, 1583.
19. (f) Gao, X.-W.; Meng, Q.-Y.; Xiang, M.; Chen, B.; Feng, K.; Tung, C.-H.; Wu, L.-Z. Adv. Synth. Catal. 2013, 355, 2158.
20. (g) Li, K.; Tan, G.; Huang, J.; Song, F.; You, J. Angew. Chem., Int. Ed. 2013, 52, 1.
21. (h) Huo, C.; Wang, C.; Wu, M.; Jia, X.; Xie, H.; Yuan, Y. Adv. Synth. Catal. 2014, 356, 411.
22. (i) Wei, W.-T.; Song, R.-J.; Li, J.-H. Adv. Synth. Catal. 2014, 356, 1703.
23. A book and reviews on quinolines: (a) Eicher, T.; Hauptmann, S.; Speicher, A. The Chemistry of Heterocycles, 2nd ed.; WILEY-VCH: 2003.
24. (b) Michael, J. P. Nat. Prod. Rep. 2003, 20, 476.
25. (c) Michael, J. P. Nat. Prod. Rep. 2008, 25, 166.
26. (a) Hibino, S.; Weinreb, S. M. J. Org. Chem. 1977, 42, 232.
27. (b) Shen, W.; Coburn, C. A.; Bornmann, W. G.; Danishefsky, S. J. J. Org. Chem. 1993, 58, 611.
28. (c) Myers, A. G.; Tom, N. J.; Fraley, M. E.; Cohen, S. B.; Madar, D. J. J. Am. Chem. Soc. 1997, 119, 6072.
29. (d) Abe, Y.; Kayakiri, H.; Satoh, S.; Inoue, T.; Sawada, Y.; Inamura, N.; Asano, M.; Aramori, I.; Hatori, C.; Sawai, H.; Oku, T.; Tanaka, H. J. Med. Chem. 1998, 41, 4062.
30. (a) Liu, J.-Y.; Niu, H.-Y.; Wu, S.; Qu, G.-R.; Guo, H.-M. Chem. Commun. 2012, 48, 9723.
31. (b) Komai, H.; Yoshino, T.; Matsunage, S.; Knai, M. Org. Lett. 2011, 13, 1706.
32. (c) Jin, J. J.; Niu, H. Y.; Qu, G. R.; Guo, H. M.; Fossey, J. S. RSC Adv. 2012, 2, 5968.
33. (d) Graves, V. B.; Shaikh, A. Tetrahedron Lett. 2013, 54, 695.
34. (e) Qian, B.; Xie, P.; Xie, Y.; Huang, H. Org. Lett. 2011, 13, 2580.
35. (f) Qian, B.; Yang, L.; Huang, H. Tetrahedron Lett. 2013, 54, 711.
36. (g) Qian, B.; Guo, S.; Shao, J.; Zhu, Q.; Yang, L.; Xia, C.; Huang, H. J. Am. Chem. Soc. 2010, 132, 3650.
37. (h) Qian, B.; Guo, S.; Xia, C.; Huang, H. Adv. Synth. Catal. 2010, 352, 3195.
38. (i) Rueping, M.; Tolstoluzhsky, N. Org. Lett. 2011, 13, 1095.
39. (a) Wang, F.-F.; Luo, C.-P.; Wang, Y.; Deng, G.; Yang, L. Org. Biomol. Chem. 2012, 10, 8605.
40. (b) Wang, F.-F.; Luo, C.-P.; Deng, G.; Yang, L. Green Chem. 2014, 16, 2428.
41. (c) Gao, X.; Zhang, F.; Deng, G.; Yang, L. Org. Lett. 2014, 16, 3664.
42. (d) Jin, J.-J.; Wang, D.-C.; Niu, H.-Y.; Wu, S.; Qu, G.-R.; Zhang, Z.-B.; Guo, H.-M. Tetrahedron 2013, 69, 6579.
43. (e) Niu, R.; Xiao, J.; Liang, T.; Li, X. Org. Lett. 2012, 14, 676.
44. (f) Li, Q.; Huang, Y.; Chen, T.; Zhou, Y.; Xu, Q.; Yin, S.-F.; Han, L.-B. Org. Lett. 2014, 16, 3672.
45. (a) Zhang, Y.-G.; Xu, J.-K.; Li, X.-M.; Tian, S.-K. Eur. J. Org. Chem. 2013, 3648.
46. (b) Gong, L.; Xing, L.-J.; Xu, T.; Zhu, X.-P.; Zhou, W.; Kang, N.; Wang, B. Org. Biomol. Chem. 2014, 12, 6557.
47. (c) Li, H.-Y.; Xing, L.-J.; Xu, T.; Wang, P.; Liu, R.-H.; Wang, B. Tetrahedron Lett. 2013, 54, 858.
48. (a) Yang, F.; Li, J.; Xie, J.; Huang, Z.-Z. Org. Lett. 2010, 12, 5214.
49. (b) Huang, X.-F.; Zhu, Z.-Q.; Huang, Z.-Z. Tetrahedron 2013, 69, 857.
50. (a) Boess, E.; Schmitz, C.; Klussmann, M. J. Am. Chem. Soc. 2012, 134, 5317.
51. (b) Tian, J.-S.; Loh, T.-P. Angew. Chem., Int. Ed. 2010, 49, 8417.
52. (c) Shi, Z.; Zhang, C.; Tang, C.; Jiao, N. Chem. Soc. Rev. 2012, 41, 3381.
53. (d) Wendlandt, A. E.; Suess, A. M.; Stahl, S. S. Angew. Chem., Int. Ed. 2011, 50, 11062.