Selectivity control by silver catalysts in the cycloisomerization of 1,6-enynes derived from propiolamides

Tetrahedron Letters

Volumn 54, Issue 8, 2013, Pages 834-839

  Koo, Jaeyoung ^a   Park, Hyun Sub ^a   Shin, Seunghoon ^a  

^a Hanyang University   (South Korea)

Author keywords

1,6 Enyne; Cycloisomerization; Gold catalysis; Propiolamide; Silver carbenoid; Silver catalysis

Indexed keywords

1,6 ENYNE DERIVATIVE; AMIDE; CARBENOID; CARBONYL DERIVATIVE; FUNCTIONAL GROUP; GOLD; PLATINUM; PROPIOLAMIDE DERIVATIVE; SILVER; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; CYCLOISOMERIZATION; ISOMERIZATION; ROOM TEMPERATURE;

ALNUS;

EID: 84872289072     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2012.11.067     Document Type: Article

References (62)

1. G.C. Lloyd-Jones Org. Biomol. Catal. 1 2002 215
2. C. Aubert, O. Buisine, and M. Malacria Chem. Rev. 102 2002 813
3. V. Michelet, P.Y. Toullec, and J.-P. Genét Angew. Chem., Int. Ed. 47 2008 4268
4. E. Soriano, and Marco-Contelles Acc. Chem. Res. 1026 2009 42
5. A.M. Echavarren, and E. Jiménez-Nuñez Top. Catal. 53 2010 924
6. P.Y. Toullec, and V. Michellet Top. Curr. Chem. 302 2011 31
7. Representative examples: B.M. Trost, and C. Pedregal J. Am. Chem. Soc. 114 1992 7292
8. Q. Zhang, and X. Lu J. Am. Chem. Soc. 122 2000 7604
9. A. Lei, J.P. Waldkirch, M. He, and X. Zhang Angew. Chem., Int. Ed. 41 2002 4526
10. B.M. Trost, and F.D. Toste J. Am. Chem. Soc. 122 2000 714
11. B.M. Trost, M.U. Frederiksen, and M.T. Rudd Angew. Chem., Int. Ed. 44 2005 6630
12. M. Méndez, M.P. Muñoz, C. Nevado, D.J. Cárdenas, and A.M. Echavarren J. Am. Chem. Soc. 123 2001 10511
13. C. Fernández-Rivas, M. Méndez, and A.M. Echavarren J. Am. Chem. Soc. 122 2000 1221
14. C. Fernández-Rivas, M. Méndez, C. Nieto-Oberhuber, and A.M. Echavarren J. Org. Chem. 67 2002 5197
15. S. Porcel, and A.M. Echavarren Angew. Chem., Int. Ed. 46 2007 2672
16. For 5-exo-dig cyclization: C. Nieto-Oberhuber, M.P. Muñoz, S. López, E. Jiménez-Nuñez, C. Nevado, E. Herrero-GóMez, M. Raducan, and A.M. Echavarren Chem. Eur. J. 12 2006 1677 (Erratum, Chem. Eur. J. 2006, 14, 5088.)
17. A. Escribano-Cuesta, P. Pérez-Galán, E. Herrero-Gómez, M. Sekine, A.A.C. Braga, F. Maseras, and A.M. Echavarren Org. Biomol. Chem. 10 2012 6105
18. N(O-)-Tethered 1,6-enynes generally undergoes 6-endo cyclization: S.I. Lee, S.M. Kim, S.Y. Kim, and Y.K. Chung Synlett 2006 2256 (Corrigendum; structural re-assignment as six-membered rings. Synlett, 2009, 1355.)
19. Y.T. Lee, Y.K. Kang, and Y.K. Chung J. Org. Chem. 74 2009 7922
20. For Bi(III)-catalyzed 1,4-diene formation: S. Fang, and Z. Wang Eur. J. Org. Chem. 2009 5505
21. For selected reviews on gold catalysis: A.S.K. Hashmi Chem. Rev. 107 2007 3180
22. A. Corma, A. Leyva-Perez, and M. Sabataer J. Chem. Rev. 111 2011 1657
23. S.Md.A. Sohel, and R.S. Liu Chem. Soc. Rev. 38 2009 2269
24. A. Fürstner Chem. Soc. Rev. 38 2009 3208
25. Z. Li, C. Brouwer, and C. He Chem. Rev. 108 2008 3239
26. A. Arcadi Chem. Rev. 108 2008 3266
27. E. Jiménez-Núñez, and A.M. Echavarren Chem. Rev. 108 2008 3326
28. D.J. Gorin, B.D. Sherry, and F.D. Toste Chem. Rev. 108 2008 3351
29. D.J. Gorin, and F.D. Toste Nature 2007 446
30. A. Fürstner, and P.W. Davies Angew. Chem., Int. Ed. 46 2007 3410
31. H.-S. Yeom, J. Koo, H. Park, Y. Wang, Y. Liang, Z.-X. Yu, and S. Shin J. Am. Chem. Soc. 134 2012 208
32. B.B. Snider, and T. Killinger J. Org. Chem. 43 1978 2161
33. T. Luo, and S.L. Schreiber Angew. Chem., Int. Ed. 46 2007 8250
34. T. Luo, M. Dai, S.-L. Zhang, and S.L. Schreiber Org. Lett. 13 2011 2834
35. T. de Haro, and C. Nevado J. Am. Chem. Soc. 132 2010 1512
36. X. Tong, M. Beller, and M.K. Tse J. Am. Chem. Soc. 129 2007 4906
37. For selected reviews on Ag-catalysis: M. Álvarez-Corral, M. Muñoz-Dorado, and I. Rodríguez-García Chem. Rev. 108 2008 3174
38. J.-M. Weibel, A. Blanc, and P. Pale Chem. Rev. 108 2008 3149
39. P. Belmont, and E. Parker Eur. J. Org. Chem. 2009 6075
40. Y. Yamamoto Chem. Rev. 108 2008 3199
41. M. Naodovic, and H. Yamamoto Chem. Rev. 108 2008 3132
42. P. Belmont M. Harmata, Silver in Organic Chemistry 2010 Wiley: Hoboken New Jersey Chapter 5
43. Recently, silver salts are increasingly recognized as π-acids for alkynes (selected examples): T.J. Harrison, and G.R. Dake Org. Lett. 6 2004 5023
44. K.-G. Ji, X.-Z. Shu, S.-C. Zhao, H.-T. Zhu, Y.-N. Niu, X.-Y. Liu, and Y.-M. Liang Org. Lett. 11 2009 3206
45. R.F. Sweis, M.P. Schramm, and S.A. Kozmin J. Am. Chem. Soc. 126 2004 7442
46. T. Godet, and P. Belmont Synlett 2008 2513
47. M.-Z. Wang, C.-Y. Zhou, and C.-M. Che Chem. Commun. 47 2011 1312
48. S. Kikuchi, K. Sekine, T. Ishida, and T. Yamada Angew. Chem., Int. Ed. 51 2012 6989
49. S. Yoshida, K. Fukui, S. Kikuchi, and T. Yamada J. Am. Chem. Soc. 132 2010 4072
50. C.H. Oh, S. Karmakar, H. Park, Y. Ahn, and J.W. Kim J. Am. Chem. Soc. 132 2010 1792
51. D. Susanti, F. Koh, A. Kusuma, P. Kothandaraman, and P.W.H. Chan J. Org. Chem. 77 2012 7166
52. For effects of silver salts in gold catalysis, see: D. Wang, R. cai, S. Sharma, J. Jirak, S.K. Thummanapelli, N.G. Akhmedov, H. Zhang, X. Liu, J.L. Petersen, and X. Shi J. Am. Chem. Soc. 134 2012 9012
53. Y. Harrak, A. Simonneau, M. Malacria, V. Gandon, and L. Fensterbank Chem. Commun. 46 2010 865
54. C. Nieto-Oberhuber, S. Lopez, and A.M. Echavarren J. Am. Chem. Soc. 127 2005 6178
55. C. Nieto-Oberhuber, M.P. Muñoz, E. Buñuel, C. Nevado, D.J. Cárdenas, and A.M. Echavarren Angew. Chem., Int. Ed. 43 2004 2402
56. C. Nieto-Oberhuber, S. Lopez, M.P. Muñoz, D.J. Cárdenas, E. Buñuel, C. Nevado, and A.M. Echavarren Angew. Chem., Int. Ed. 44 2005 6146
57. Yet several tri-coordinate Au(I) complexes have been isolated, although their role as catalytically active species is unclear due to possible disproportionation: G.A. Bowmaker, J.C. Dyason, P.C. Healy, L.M. Engelhardt, C. Pakawatchai, and A.H. White J. Chem. Soc., Dalton Trans. 1987 1089
58. H.l. Ito, K. Takagi, T. Miyahara, and M. Sawamura Org. Lett. 7 2005 3001
59. Recently, tri-coordinate Au(I) complex was also implied as a catalytic intermediate J.-H. Zhan, H. Lv, Y. Yu, and J.-L. Zhang Adv. Synth. Catal. 354 2012 1529
60. Y. Luo, K. Ji, Y. Li, and L. Zhang J. Am. Chem. Soc. 2012 http://dx.doi.org/10.1021/ja307948m
61. V.W.W. Yam, and E.C.C. Cheng R.H. Crabtree, D.M.P. Mingos, Comprehensive Organometallic Chemistry III Vol. 2 2007 Elsevier Oxford Chapter 2.04
62. A similar type of intermediate to III′ has been proposed in the Ru-catalyzed redox isomerization of propargyl alcohol: B.M. Trost, A. Breder, M. O'Keefe, M. Rao, and A.W. Franz J. Am. Chem. Soc. 133 2011 4766 In the Ag-catalyzed cycloisomerization of allylsilanes/allylstannanes, the authors proposed a Ag-carbenoid as an intermediate. (Scheme 1B, Ref. 4c)