Gold-catalyzed multiple cascade reaction of 2-alkynylphenylazides with propargyl alcohols

Chemistry - A European Journal

Volumn 21, Issue 9, 2015, Pages 3585-3588

  Li, Nan ^a   Wang, Tian Yi ^a   Gong, Liu Zhu ^a   Zhang, Liming ^b  

^a UNIVERSITY OF SCIENCE AND TECHNOLOGY OF CHINA   (China)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Carbenes; Cascade reactions; Chirality transfer; Gold catalysis; Sigmatropic rearrangement

Indexed keywords

CATALYSIS; CHIRALITY; GOLD; SYNTHESIS (CHEMICAL);

CARBENES; CASCADE REACTIONS; CHIRALITY TRANSFER; GOLD CATALYSIS; SIGMATROPIC REARRANGEMENTS;

GOLD COMPOUNDS;

EID: 84922998558     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201406456     Document Type: Article

References (56)

1. a) R. Robinson, J. Chem. Soc. Trans. 1917, 111, 762;
2. b) W. S. Johnson, M. B. Gravestock, B. E. McCarry, J. Am. Chem. Soc. 1972, 94, 4332;
3. K. C. Nicolaou, N. A. Petasis, R. E. Zipkin, J. Uenishi, J. Am. Chem. Soc. 1971, 93, 4332.
4. a) K. C. Nicolaou, D. J. Edmonds, P. G. Bulger, Angew. Chem. Int. Ed. 2006, 45, 7134;
5. Angew. Chem. 2006, 118, 7292;
6. b) K. C. Nicolaou, J. S. Chen, Chem. Soc. Rev. 2009, 38, 2993;
7. C. Grondal, M. Jeanty, D. Enders, Nat. Chem. 2010, 2, 167;
8. L.-Q. Lu, J.-R. Chen, W.-J. Xiao, Acc. Chem. Res. 2012, 45, 1278;
9. e) L. F. Tietze, G. Brasche, K. Gericke, Domino Reactions in Organic Synthesis Wiley-VCH, Weinheim, 2006;
10. f) Metal Catalyzed Cascade Reactions (Ed.: T. J. J. Müller), Springer, 2006;
11. g) Catalytic Cascade Reactions (Eds.: P.-F. Xu, W. Wang), Wiley, Hoboken, 2013.
12. a) A. S. K. Hashmi, Chem. Rev. 2007, 107, 3180;
13. b) D. J. Gorin, F. D. Toste, Nature 2007, 446, 395;
14. Z. Li, C. Brouwer, C. He, Chem. Rev. 2008, 108, 3239;
15. A. Arcadi, Chem. Rev. 2008, 108, 3266;
16. e) D. J. Gorin, B. D. Sherry, F. D. Toste, Chem. Rev. 2008, 108, 3351;
17. f) A. S. K. Hashmi, Acc. Chem. Res. 2014, 47, 864;
18. g) H.-S. Yeom, S. Shin, Acc. Chem. Res. 2014, 47, 966;
19. h) L. Zhang, Acc. Chem. Res. 2014, 47, 877;
20. C. Obradors, A. M. Echavarren, Acc. Chem. Res. 2014, 47, 902.
21. D. J. Gorin, N. R. Davis, F. D. Toste, J. Am. Chem. Soc. 2005, 127, 11260.
22. a) Z.-Y. Yan, Y. Xiao, L. Zhang, Angew. Chem. Int. Ed. 2012, 51, 8624;
23. Angew. Chem. 2012, 124, 8752;
24. b) Y. Xiao, L. Zhang, Org. Lett. 2012, 14, 4662.
25. C. Gronnier, G. Boissonnat, F. Gagosz, Org. Lett. 2013, 15, 4234.
26. a) A. Wetzel, F. Gagosz, Angew. Chem. Int. Ed. 2011, 50, 7354;
27. Angew. Chem. 2011, 123, 7492;
28. b) B. Lu, Y. Luo, L. Liu, L. Ye, Y. Wang, L. Zhang, Angew. Chem. Int. Ed. 2011, 50, 8358;
29. Angew. Chem. 2011, 123, 8508.
30. a) G. Saucy, L. H. Chopard-dit-Jean, W. Guex, G. Ryser, O. Isler, Helv. Chim. Acta 1958, 41, 160;
31. b) R. Marbet, G. Saucy, Chimia 1960, 14, 362;
32. G. Saucy, R. Marbet, Helv. Chim. Acta 1967, 50, 1158.
33. B. D. Sherry, F. D. Toste, J. Am. Chem. Soc. 2004, 126, 15978.
34. a) N. T. Patil, L. M. Lutete, N. Nishina, Y. Yamamoto, Tetrahedron Lett. 2006, 47, 4749;
35. b) R. L. LaLonde, B. D. Sherry, E. J. Kang, F. D. Toste, J. Am. Chem. Soc. 2007, 129, 2452;
36. R. E. Kinder, Z. Zhang, R. A. Widenhoefer, Org. Lett. 2008, 10, 3157;
37. K. L. Butler, M. Tragni, R. A. Widenhoefer, Angew. Chem. Int. Ed. 2012, 51, 5175;
38. Angew. Chem. 2012, 124, 5265;
39. e) M. C. M. Higginbotham, M. W. P. Bebbington, Chem. Commun. 2012, 48, 7565;
40. f) D. Pflästerer, P. Dolbundalchok, S. Rafique, M. Rudolph, F. Rominger, A. S. K. Hashmi, Adv. Synth. Catal. 2013, 355, 1383.
41. a) A. Karadeolian, M. A. Kerr, Angew. Chem. Int. Ed. 2010, 49, 1133;
42. Angew. Chem. 2010, 122, 1151;
43. b) A. Karadeolian, M. A. Kerr, J. Org. Chem. 2010, 75, 6830;
44. J. Lee, J. S. Panek, Org. Lett. 2011, 13, 502;
45. X. Zhang, T. Mu, F. X. Zhan, L. J. Ma, G. X. Liang, Angew. Chem. Int. Ed. 2011, 50, 6164;
46. Angew. Chem. 2011, 123, 6288;
47. e) W. Wu, M. Xiao, J. Wang, Y. Li, Z. Xie, Org. Lett. 2012, 14, 1624.
48. a) C. Nieto-Oberhuber, S. López, A. M. Echavarren, J. Am. Chem. Soc. 2005, 127, 6178;
49. b) C. Nieto-Oberhuber, M. P. Muñoz, S. López, E. Jiménez-Núñez, C. Nevado, E. Herrero-Gómez, M. Raducan, A. M. Echavarren, Chem. Eur. J. 2006, 12, 1677.
50. a) N. M. Scott, S. P. Nolan, Eur. J. Inorg. Chem. 2005, 1815;
51. b) W. A. Herrmann, J. Schütz, G. D. Frey, E. Herdtweck, Organometallics 2006, 25, 2437;
52. N. Marion, S. P. Nolan, Acc. Chem. Res. 2008, 41, 1440;
53. J. C. Y. Lin, R. T. W. Huang, C. S. Lee, A. Bhattacharyya, W. S. Hwang, I. J. B. Lin, Chem. Rev. 2009, 109, 3561;
54. e) Y. Chi, P. T. Chou, Chem. Soc. Rev. 2010, 39, 638;
55. f) H. Clavier, S. P. Nolan, Chem. Commun. 2010, 46, 841;
56. g) S. P. Nolan, Acc. Chem. Res. 2011, 44, 91.