Highly regioselective Au(I)-Catalyzed hydroamination of ynamides and propiolic acid derivatives with anilines

Organic Letters

Volumn 11, Issue 18, 2009, Pages 4208-4211

  Kramer, Soren ^a   Dooleweerdt, Karin ^a   Lindhardt, Anders Thyboe ^a   Rottländer, Mario ^b   Skrydstrup, Troeis ^a  

^a AARHUS UNIVERSITY   (Denmark)

^b H LUNDBECK A S   (Denmark)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE; ANILINE; ANILINE DERIVATIVE; GOLD; PROPIOLIC ACID; PROPIONIC ACID DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; CYCLIZATION; STEREOISOMERISM;

ALKYNES; ANILINE COMPOUNDS; CATALYSIS; COMBINATORIAL CHEMISTRY TECHNIQUES; CYCLIZATION; GOLD; MOLECULAR STRUCTURE; PROPIONATES; STEREOISOMERISM;

EID: 70349140103     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol901565p     Document Type: Article

References (67)

1. Hydroaminations. Gold: (a) Mizushima, E.; Hayashi, T.; Tanaka, M. Org. Lett. 2003, 5, 3349.
2. (b) Bertrand, G.; Donnadieu, B.; Kinjo, R.; Frey, G. D.; Zeng, X. J. Am. Chem. Soc. 2009, 131, 8690.
3. (c) Zeng, X.; Frey, G. D.; Kousar, S.; Bertrand, G. Chem.-Eur. J. 2009, 15, 3056.
4. (d) Widenhoefer, R. A.; Han, X. Eur. J. Org. Chem. 2006, 4555.
5. (e) Liu, X.Y.; Ding, P.; Huang, J.-S.; Che, C.-M. Org. Lett. 2007, 9, 2645. Titanium:
6. (f) Synthesis 2005, 7, 1200.
7. (g) Ackermann, L. Organometallics 2003, 22, 4367.
8. (h) Schafer, L. L.; Zhang, Z. Org. Lett. 2003, 5, 4733.
9. (i) Bytschkov, I.; Siebeneicher, H.; Doye, S. Eur. J. Org. Chem. 2003, 2888.
10. (j) Cao, C.; Shi, Y.; Odom, A. L. Org. Lett. 2002, 4, 2853.
11. (k) Ackermann, L.; Born, R. Tetrahedron Lett. 2004, 9541.
12. (l) Cao, C.; Ciszewski, J. T.; Odom, A. L. Organometallics 2001, 20, 5011. Palladium.:
13. (m) Shimada, T.; Yamamoto, Y. J. Am. Chem. Soc 2002, 124, 12670.
14. (n) Shi, Z.; Zhang, C.; Li, S.; Pan, D.; Ding, S.; Cui, Y.; Jiao, N. Angew. Chem., Int. Ed. 2009, 48, 4572. Cobalt:
15. (o) Liu, C.-C.; Korivi, R. P.; Cheng, C.-H. Chem.-Eur. J. 2008, 14, 9503. Silver:
16. (p) Lingaiah, N.; Babu, N. S.; Reddy, K. M.; Prasad, P. S. S.; Suryanarayana, I. Chem. Commun. 2007, 278.
17. (q) Luo, Y.; Li, Z.; Li, C.-J. Org. Lett. 2005, 7, 2675. Tantalum.:
18. (r) Bergman, R. G.; Arnold, J.; Anderson, L. L. Org. Lett. 2004, 6, 2519. Review:
19. (s) Alonso, F.; Beletskaya, I. P.; Yus, M. Chem. Rev. 2004, 6, 3079.
20. Gold-catalyzed hydrations: (a) Corma, A.; Leyva, A. J. Org. Chem. 2009, 74, 2067.
21. (b) Mizushima, E.; Sato, K.; Hayashi, T.; Tanaka, M. Angew. Chem., Int. Ed. 2002, 41, 4563.
22. Mézailles, N.; Ricard, L.; Gagosz, F. Org. Lett. 2005, 7, 4133.
23. For a special issue dedicated ynamides, see: (a) TetrahedronSymposium-In- Print: "Chemistry of Electron-Deficient Ynamines and Ynamides." Tetrahedron 2006, 62, Issue No. 16. For reviews on ynamides, see:
24. (b) Zificsak, C. A.; Mulder, J. A.; Hsung, R. P.; Rameshkumar, C.; Wei, L. L. Tetrahedron 2001, 57, 7575.
25. (c) Zhang, Y.; Hsung, R. P. ChemTracts 2004, 17, 442.
26. (d) Katritzky, A. R.; Jiang, R.; Singh, S. K. Heterocycles 2004, 63, 1455.
27. For some recent examples, see: (a) Dooleweerdt, K.; Ruhland, T.; Skrydstrup, T. Org. Lett. 2009, 11, 221.
28. (b) Gourdet, B.; Lam, H. W. J. Am. Chem. Soc. 2009, 131, 3802.
29. (c) Saito, N.; Katayama, T.; Sato, Y. Org. Lett. 2008, 10, 3829.
30. (d) Istrate, F. M.; Buzas, A. K.; Jurberg, I. D.; Odabachian, Y.; Gagosz, F. Org. Lett. 2008, 10, 925.
31. (e) Hashmi, S. K.; Rudolph, M.; Bats, J. W.; Frey, W.; Rominger, F.; Oeser, T. Chem.-Eur. J. 2008, 14, 6672.
32. (f) Couty, S.; Meyer, C.; Cossy, J. Synlett 2007, 2819.
33. (g) Tanaka, K.; Takeishi, K. Synlett 2007, 2920.
34. (h) Kohnen, A. L.; Mak, X. Y.; Lam, T. Y.; Dunetz, J. R.; Danheiser, R. L. Tetrahedron 2006, 62, 3815.
35. (h) Couty, S.; Meyer, C.; Cossy, J. Angew. Chem., Int. Ed. 2006, 45, 6726.
36. (i) Tanaka, K.; Takeishi, K.; Noguchi, K. J. Am. Chem. Soc. 2006, 128, 4586.
37. Recent applications of ynamides from the group of R. P. Hsung: (a) Zhang, Y.; DeKorver, K. A.; Lohse, A. G.; Zhang, Y.-S.; Huang, J.; Hsung, R. P. Org. Lett. 2009, 11, 899.
38. (b) Oppenheimer, J.; Johnson, W. L.; Figueroa, R.; Hayashi, R.; Hsung, R. P. Tetrahedron 2009, 65, 5001.
39. (c) Yao, P.-Y.; Zhang, Y.; Hsung, R. P.; Zhao, K. Org. Lett. 2008, 10, 4215.
40. (d) Al-Rashid, Z. F.; Johnson, W. L.; Hsung, R. P.; Wei, Y.; Yao, P.-Y.; Liu, R.; Zhao, K. J. Org. Chem. 2008, 73, 8780.
41. (e) Zhang, X.; Hsung, R. P.; Li, H.; Zhang, Y.; Johnson, W. L.; Figueroa, R. Org. Lett. 2008, 10, 3411.
42. (f) Al-Rashid, Z. F.; Hsung, R. P. Org. Lett. 2008, 10, 661.
43. (g) Li, H.; You, L.; Zhang, X.; Johnson, W. L.; Figueroa, R.; Hsung, R. P. Heterocycles 2007, 74, 553.
44. (h) You, L.; Al-Rashid, Z. F.; Figueroa, R.; Ghosh, S. K.; Li, G.; Lu, T.; Hsung, R. P. Synlett 2007, 1656.
45. (i) Oppenheimer, J.; Johnson, W. L.; Tracey, M. R.; Hsung, R. P.; Yao, P.-Y.; Liu, R.; Zhao, K. Org. Lett. 2007, 9, 2361.
46. (j) Song, Z.; Lu, T.; Hsung, R. P.; Al-Rashid, Z. F.; Ko, C.; Tang, Y. Angew. Chem., Int. Ed. 2007, 46, 4069.
47. (k) Zhang, X.; Hsung, R. P.; Li, H. Chem.Commun. 2007, 23, 2420.
48. (a) Yao, B.; Liang, Z.; Niu, T.; Zhang, Y. J. Org. Chem. 2009, 74, 4630.
49. (b) Coste, A.; Karthikeyan, G.; Couty, F.; Evano, G. Angew. Chem., Int., Ed. 2009, 48, 4381.
50. (c) Hamada, T.; Ye, X.; Stahl, S. S. J. Am. Chem. Chem. 2008, 130, 833.
51. (d) Dooleweerdt, K.; Birkedal, H.; Ruhland, T.; Skrydstrup, T. J. Org. Chem. 2008, 73, 9447.
52. (e) Riddell, N.; Villeneuve, K.; Tam, W. Org. Lett. 2005, 7, 3681.
53. (f) Sagamanova, I. K.; Kurtz, K. C. M.; Hsung, R. P. Org. Synth. 2007, 84, 359.
54. (g) Zhang, X.; Zhang, Y.; Huang, J.; Hsung, R. P.; Kurtz, K. C. M.; Oppenheimer, J.; Petersen, M. E.; Sagamanova, I. K.; Shen, L.; Tracey, M. R. Org. Chem. 2006, 71, 4170.
55. (h) Kohnen, A. L.; Dunetz, J. R.; Danheiser, R. L. Org. Synth. 2007, 84, 88.
56. (i) For reviews on the synthesis of ynamides, see: Mulder, J. A.; Kurtz, K. C. M.; Hsung, R. P. Synlett 2003, 1379.
57. Selected reviews on Au catalysis: (a) Gorin, D. J.; Toste, D. Nature 2007, 446, 395.
58. (b) Li, Z.; Brouwer, C.; He, C. Chem.Rev. 2008, 108, 3239.
59. (c) Hashmi, A. S. K. Chem. Rev. 2007, 107, 3180.
60. (d) Fürstner, A.; Davies, P. W. Angew. Chem., Int. Ed. 2007, 46, 3410.
61. (e) Arcadi, A. Chem. Rev. 2008, 108, 3266.
62. As the imine functionality of 2a was found to be the E-isomer (Figure 1) and only one isomer was observed in all the reactions, the products 2b-k reported were tentatively assigned this configuration.
63. Due to the ynamides utilized being either sulfonamides or cyclic carbamates no conversion to the oxazolone products as reported by Gagosz et al. were observed (ref 5d).
64. 1H NMR and by comparison with, the known compound. LópezAlberca, M. P.; Mancheño, M. J.; Fernández, I.; Gómez-Gallengo, M.; Sierra, M. A.; Torres, R. Org. Lett. 2007, 9, 1757. The regioselectivity of 3e was confirmed by acid hydrolysis.
65. Several attempts to develop a one-pot protocol for the hydroamination and ensuing Pd(O)-catalyzed cyclization were unsuccesful. In these cases, it was necessary to purify the intermediates in order to secure good cyclization yields.
66. Larock, R. C.; Yum, E. K. J. Am. Chem. Soc. 1991, 113, 6689.
67. Yu, W.; Du, Y.; Zhao, K. Org. Lett. 2009, 11, 2417.