Regioselective cyclizations utilizing a gold-catalyzed [3,3] propargyl ester rearrangement

Angewandte Chemie - International Edition

Volumn 51, Issue 37, 2012, Pages 9398-9402

  Cran, John W ^a   Krafft, Marie E ^a  

^a FLORIDA STATE UNIVERSITY   (United States)

Author keywords

carbocycles; gold; rearrangement; regioselectivity; synthetic methods

Indexed keywords

CARBOCYCLES; CHEMOSELECTIVE; CYCLIZATIONS; PROPARGYL; PROPARGYLIC ESTER; REARRANGEMENT; REGIO-SELECTIVE; REGIOCHEMISTRY; REGIOSELECTIVE SYNTHESIS; SIGMATROPIC REARRANGEMENTS; SYNTHETIC METHODS;

CATALYSIS; ESTERIFICATION; ESTERS; GOLD;

REGIOSELECTIVITY;

EID: 84865853394     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201203923     Document Type: Article

References (65)

1. J. K. Ergüden, H. W. Moore, Org. Lett. 1999, 1, 375
2. L.-C. Wang, A. L. Luis, K. Agapiou, H.-Y. Jang, M. J. Krische, J. Am. Chem. Soc. 2002, 124, 2402
3. S. A. Frank, D. J. Mergott, W. R. Roush, J. Am. Chem. Soc. 2002, 124, 2404. For enantioselective variants, see
4. C. E. Aroyan, S. J. Miller, J. Am. Chem. Soc. 2007, 129, 256
5. F. Seidel, J. A. Gladysz, Synlett 2007, 986
6. E. Marqués-López, R. P. Herrera, T. Marks, W. C. Jacobs, D. Könning, R. M. de Figueiredo, M. Christmann, Org. Lett. 2009, 11, 4116.
7. M. Rauhut, H. Currier, (American Cyanamid Co.), US Patent 307,499,919,630,122, 1963 [Chem. Abstr. 1963, 58, 11224a].
8. For a recent review, see:, C. E. Aroyan, A. Dermenci, S. J. Miller, Tetrahedron 2009, 65, 4069.
9. K. Agapiou, M. J. Krische, Org. Lett. 2003, 5, 1737
10. J. L. Methot, W. R. Roush, Org. Lett. 2003, 5, 4223
11. M. Lorenz, W. Boland, K. Dettner, Angew. Chem. 1993, 105, 904
12. Angew. Chem. Int. Ed. Engl. 1993, 32, 912.
13. M. E. Krafft, T. F. N. Haxell, K. A. Seibert, K. A. Abboud, J. Am. Chem. Soc. 2006, 128, 4174
14. J. W. Cran, M. E. Krafft, K. A. Seibert, T. F. N. Haxell, J. A. Wright, C. Hirosawa, K. A. Abboud, Tetrahedron 2011, 67, 9922.
15. L. Zhang, J. Am. Chem. Soc. 2005, 127, 16804.
16. S. Wang, G. Zhang, L. Zhang, Synlett 2010, 692. For general reviews on gold-based catalysis in organic synthesis, see
17. Z. Li, C. Brouwer, C. He, Chem. Rev. 2008, 108, 3239
18. A. Arcadi, Chem. Rev. 2008, 108, 3266
19. E. Jiménez-Núñez, A. M. Echavarren, Chem. Rev. 2008, 108, 3326
20. D. J. Gorin, B. D. Sherry, F. D. Toste, Chem. Rev. 2008, 108, 3351
21. N. T. Patil, Y. Yamamoto, Chem. Rev. 2008, 108, 3395
22. A. S. K. Hashmi, M. Rudolph, Chem. Soc. Rev. 2008, 37, 1766
23. A. Fürstner, P. W. Davis, Angew. Chem. 2007, 119, 3478
24. Angew. Chem. Int. Ed. 2007, 46, 3410. For reviews covering gold-catalyzed propargyl esters rearrangements, see
25. N. Marion, S. P. Nolan, Angew. Chem. 2007, 119, 2806
26. Angew. Chem. Int. Ed. 2007, 46, 2750
27. J. Marco-Contelles, E. Soriano, Chem. Eur. J. 2007, 13, 1350.
28. K. Miki, K. Ohe, S. Uemura, J. Org. Chem. 2003, 68, 8505
29. V. Mamane, T. Gress, H. Krause, A. Fürstner, J. Am. Chem. Soc. 2004, 126, 8654
30. X. Shi, D. J. Gorin, F. D. Toste, J. Am. Chem. Soc. 2005, 127, 5802
31. M. J. Johansson, D. J. Gorin, S. T. Staben, F. D. Toste, J. Am. Chem. Soc. 2005, 127, 18002.
32. A. Correa, N. Marion, L. Fensterbank, M. Malacria, S. P. Nolan, L. Cavallo, Angew. Chem. 2008, 120, 730
33. Angew. Chem. Int. Ed. 2008, 47, 718.
34. G. Li, G. Zhang, L. Zhang, J. Am. Chem. Soc. 2008, 130, 3740, and references therein.
35. L. Zhang, S. Wang, J. Am. Chem. Soc. 2006, 128, 1442
36. N. Marion, S. Díez-González, P. de Frémont, A. R. Noble, S. P. Nolan, Angew. Chem. 2006, 118, 3729
37. Angew. Chem. Int. Ed. 2006, 45, 3647
38. J. Zhao, C. O. Hughes, F. D. Toste, J. Am. Chem. Soc. 2006, 128, 7436-7437
39. C. H. Oh, A. Kim, W. Park, D. I. Park, N. Kim, Synlett 2006, 2781
40. S. Wang, L. Zhang, J. Am. Chem. Soc. 2006, 128, 8414
41. S. Wang, L. Zhang, Org. Lett. 2006, 8, 4585
42. A. Buzas, F. Gagosz, J. Am. Chem. Soc. 2006, 128, 12614
43. M. Yu, G. Zhang, L. Zhang, Org. Lett. 2007, 9, 2147
44. T. Luo, S. L. Schreiber, Angew. Chem. 2007, 119, 8398
45. Angew. Chem. Int. Ed. 2007, 46, 8250
46. C. H. Oh, A. Kim, New J. Chem. 2007, 31, 1719
47. C. H. Oh, A. Kim, Synlett 2008, 777
48. L. Cui, G. Zhang, L. Zhang, Bioorg. Med. Chem. Lett. 2009, 19, 3884
49. D. Lebœuf, A. Simonneau, C. Aubert, M. Malacria, V. Gandon, L. Fensterbank, Angew. Chem. 2011, 123, 7000
50. Angew. Chem. Int. Ed. 2011, 50, 6868.
51. A. S. K. Hashmi, L. Schwarz, J.-H. Choi, T. M. Frost, Angew. Chem. 2000, 112, 2382
52. Angew. Chem. Int. Ed. 2000, 39, 2285
53. M. Alfonsi, A. Arcadi, M. Aschi, G. Bianchi, F. Marinelli, J. Org. Chem. 2005, 70, 2265. However, the role of gold in these cases is unclear; see
54. A. S. K. Hashmi, L. Schwarz, P. Rubenbauer, M. C. Blanco, Adv. Synth. Catal. 2006, 348, 705
55. A. S. K. Hashmi, T. D. Ramamurthi, F. Rominger, J. Organomet. Chem. 2009, 694, 592.
56. E. M. W. Janssen, J. C. W. Folmer, G. A. Wiegers, J. Less-Common Met. 1974, 38, 71
57. A. Vogler, H. Kunkely, Coord. Chem. Rev. 2001, 219-221, 489
58. G. Lemière, V. Gandon, N. Agenet, J.-P. Goddard, A. Kozak, C. Aubert, L. Fensterbank, M. Malacria, Angew. Chem. 2006, 118, 7758
59. Angew. Chem. Int. Ed. 2006, 45, 7596.
60. A. R. Hardin, R. Sarpong, Org. Lett. 2007, 9, 4547
61. K. Cariou, E. Mainetti, L. Fensterbank, M. Malacria, Tetrahedron 2004, 60, 9745.
62. Y. Wang, B. Lu, L. Zhang, Chem. Commun. 2010, 46, 9179.
63. P. Mauleón, J. L. Krinsky, F. D. Toste, J. Am. Chem. Soc. 2009, 131, 4513
64. G. Lemière, V. Gandon, K. Cariou, A. Hours, T. Fukuyama, A-;L. Dhimane, L. Fensterbank, M. Malacria, J. Am. Chem. Soc. 2009, 131, 2993
65. D. Garayalde, E. Gómez-Bengoa, X. Huang, A. Goeke, C. Nevado, J. Am. Chem. Soc. 2010, 132, 4720.