Regio- and stereoselective Au(I)-catalyzed intermolecular hydroalkoxylation of aryl allenes

Synlett

Volumn , Issue 7, 2009, Pages 1103-1106

  Cui, Dong Mei ^a   Yu, Ke Rui ^a   Zhang, Chen ^b  

^a ZHEJIANG UNIVERSITY OF TECHNOLOGY   (China)

^b ZHEJIANG UNIVERSITY   (China)

Author keywords

Alcohols; Allenes; Catalysis; Hydroalkoxylation; Regioselectivity; Stereoselectivity

Indexed keywords

ALLENE DERIVATIVE; ALLYLIC ETHER DERIVATIVE; ARYL ALLENE DERIVATIVE; ETHER DERIVATIVE; GOLD COMPLEX; SULFURIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; HYDROALKOXYLATION; STEREOCHEMISTRY; SYNTHESIS;

EID: 67649418185     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0028-1088158     Document Type: Article

References (47)

1. Recent reviews, see: (a) Skouta, R.; Li, C.-J. Tetrahedron 2008, 64, 4917.
2. (b) Shen, H. C. Tetrahedron 2008, 64, 3885.
3. (c) Muzart, J. Tetrahedron 2008, 64, 3815.
4. (d) Hashmi, A. S. K. Chem. Rev. 2007, 107, 3180.
5. (e) Hashmi, A. S. K. Gold Bull. 2004, 37, 51.
6. (f) Arcadi, A.; Di Giuseppe, S. Curr. Org. Chem. 2004, 8, 795.
7. For examples, see: (a) Skouta, R.; Li, C. J. Angew. Chem. Int. Ed. 2007, 46, 1117.
8. (b) Dube, P.; Toste, F. D. J. Am. Chem. Soc. 2006, 128, 12062.
9. (c) Casado, R.; Contel, M.; Laguna, M.; Romero, P.; Sanz, S. J. Am. Chem. Soc. 2003, 125, 11925.
10. (d) Gonzalez-Arellano, C.; Abad, A.; Corma, A.; Garcia, H.; Iglesias, M.; Sanchez, F. Angew. Chem. Int. Ed. 2007, 46, 1536.
11. (e) Zhang, Z. B.; Widenhoefer, R. A. Angew. Chem. Int. Ed. 2007, 46, 283.
12. (f) Hashmi, A. S. K.; Weyrauch, J. P.; Kurpejovi, E.; Frost, T. M.; Miehlich, B.; Frey, W.; Bats, J. W. Chem. Eur. J. 2006, 12, 5806.
13. (g) LaLonde, R. L.; Sherry, B. D.; Kang, E. J.; Toste, F. D. J. Am. Chem. Soc. 2006, 129, 2452.
14. (h) Mézailles, N.; Ricard, L.; Gagosz, F. Org. Lett. 2005, 7, 4133.
15. (i) Mézailles, N.; Ricard, L.; Gagosz, F. Org. Lett. 2005, 7, 4133.
16. (a) Genin, E.; Toullec, P. Y.; Antoniotti, S.; Brancour, C.; Genêt, J.-P.; Michelet, V. J. Am. Chem. Soc. 2006, 128, 3112.
17. (b) Sun, J.; Conley, M. P.; Zhang, L.; Kozmin, S. A. J. Am. Chem. Soc. 2006, 128, 9705.
18. (c) Sherry, B. D.; Maus, L.; Laforteza, B. N.; Toste, F. D. J. Am. Chem. Soc. 2006, 128, 8132.
19. (d) Fukuda, Y.; Utimoto, K. J. Org. Chem. 1991, 56, 3729.
20. (e) Fukuda, Y.; Utimoto, K. Bull. Chem. Soc. Jpn. 1991, 64, 203.
21. (f) Mizushima, E.; Sato, K.; Hayashi, T.; Tanaka, M. Angew. Chem. Int. Ed. 2002, 41, 4563.
22. (g) Roembke, P.; Schmidbaur, H.; Cronje, S.; Raubenheimer, H. J. Mol. Catal. A: Chem. 2004, 212, 35.
23. (h) Mizushima, E.; Cui, D.-M.; Nath, D. C. D.; Hayashi, T.; Tanaka, M. Org. Synth. 2006, 83, 55.
24. (i) Mizushima, E.; Sato, K.; Hayashi, T.; Tanaka, M. Org. Lett. 2003, 5, 3349.
25. (a) Olsson, L.-I.; Claesson, A. Synthesis 1979, 743.
26. (b) Marshall, J. A.; Wolf, M. A.; Wallace, E. M. J. Org. Chem. 1997, 62, 367.
27. (c) Deutsch, C.; Gockel, B.; Hoffmann-Röder, A.; Krause, N. Synlett 2007, 1790.
28. (d) Hamilton, G. L.; Kang, E. J.; Mba, M.; Toste, F. D. Science 2007, 317, 496.
29. (e) Volz, F.; Krause, N. Org. Biomol. Chem. 2007, 5, 1519.
30. (f) Hashmi, A. S. K.; Blanco, M. C.; Fischer, D.; Bats, J. W. Eur. J. Org. Chem. 2006, 1387.
31. (g) Erdsak, J.; Krause, N. Synthesis 2007, 3741.
32. (h) Alcaide, B.; Almendros, P.; Martinez del Campo, T. Angew. Chem. Int. Ed. 2007, 46, 6684.
33. (i) Zhang, Z.; Liu, C.; Kinder, R. E.; Han, X.; Qian, H.; Widenhoefer, R. A. J. Am. Chem. Soc. 2006, 128, 9066.
34. (j) Zhang, Z.; Widenhoefer, R. A. Angew. Chem. Ind. Ed. 2007, 46, 283.
35. (k) Hoffmann-Röder, A.; Krause, N. Org. Lett. 2001, 3, 2537.
36. (l) Gockel, B.; Krause, N. Org. Lett. 2006, 8, 4485.
37. (m) Walkup, R. D.; Park, G. Tetrahedron Lett. 1987, 28, 1023.
38. (n) Ma, S.; Yu, Z.; Wu, S. Tetrahedron 2001, 57, 1585.
39. (o) Yu, X.; Seo, S.-Y.; Marks, T. J. J. Am. Chem. Soc. 2007, 129, 7244.
40. (a) Fukuda, Y.; Utimoto, K. J. Org. Chem. 1991, 56, 3729.
41. (b) Fukuda, Y.; Utimoto, K. JP 04095039, 1992; Chem. Abstr. 1992, 117, 191330.
42. Zhang, Z.; Widenhoefer, R. A. Org. Lett. 2008, 10, 2079.
43. Nishina, N.; Yamamoto, Y. Tetrahedron Lett. 2008, 49, 1023.
44. (a) Zhang, C.; Cui, D.-M.; Yao, L.-Y.; Wang, B.-S.; Hu, Y.-Z.; Hayashi, T. J. Org. Chem. 2008, 73, 7811.
45. (b) Cui, D.-M.; Zheng, Z.-L.; Zhang, C. J. Org. Chem. 2009, 74, 1426.
46. (c) Cui, D.-M.; Meng, Q.; Zheng, J.-Z.; Zhang, C. Chem. Commun. 2009, DOI: 10.1039/b818863g.
47. 3): δ = 7.29 (d, J = 8.0 Hz, 2 H), 7.11 (d, J = 8.0 Hz, 2 H), 6.57 (d, J = 15.5 Hz, 1 H), 6.25 (dt, J = 15.5, 6.0 Hz, 1 H),