A silver(I)-catalyzed tandem reaction of 2-alkynylbenzaldoxime with alkylidenecyclopropane

Organic Letters

Volumn 14, Issue 13, 2012, Pages 3430-3433

  Xiao, Qian ^a,b   Ye, Shengqing ^a   Wu, Jie ^a,c  

^a FUDAN UNIVERSITY   (China)

^b NANCHANG UNIVERSITY   (China)

^c SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPROPANE DERIVATIVE; FUSED HETEROCYCLIC RINGS; ORGANOMETALLIC COMPOUND; OXIME; SILVER;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

BICYCLO COMPOUNDS, HETEROCYCLIC; CATALYSIS; CYCLOPROPANES; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; OXIMES; SILVER; STEREOISOMERISM;

EID: 84863607185     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol301393f     Document Type: Article

References (70)

1. Armstrong, A.; Collins, J. C. Angew. Chem., Int. Ed. 2010, 49, 2282
2. Katritzky, A. R.; Rachwal, S. Chem. Rev. 2010, 110, 1564
3. Martins, M. A. P.; Frizzo, C. P.; Moreira, D. N.; Buriol, L.; Machado, P. Chem. Rev. 2009, 109, 4140
4. Alvarez-Corral, M.; Munoz-Dorado, M.; Rodriguez-Garcia, I. Chem. Rev. 2008, 108, 3174
5. Minatti, A.; Muniz, K. Chem. Soc. Rev. 2007, 36, 1142
6. Zeni, G.; Larock, R. C. Chem. Rev. 2006, 106, 4644
7. Ruijter, E.; Scheffelaar, R.; Orru, R. V. A. Angew. Chem., Int. Ed. 2011, 50, 6234
8. Walsh, D. P.; Chang, Y.-T. Chem. Rev. 2006, 106, 2476
9. Arya, P.; Chou, D. T. H.; Baek, M.-G. Angew. Chem., Int. Ed. 2001, 40, 339
10. Schreiber, S. L. Science 2000, 287, 1964
11. Burke, M. D.; Schreiber, S. L. Angew. Chem., Int. Ed. 2004, 43, 46
12. Schreiber, S. L. Nature 2009, 457, 153
13. Tan, D. S. Nat. Chem. Biol. 2005, 1, 74
14. Cordier, C.; Morton, D.; Murrison, S.; Nelson, A.; O'Leary-Steele, C. Nat. Prod. Rep. 2008, 25, 719
15. Montgomery, J. Angew. Chem., Int. Ed. 2004, 43, 3890
16. Negishi, E.; Coperet, C.; Ma, S.; Liou, S. Y.; Liu, F. Chem. Rev. 1996, 96, 365
17. Tietze, L. F. Chem. Rev. 1996, 96, 115
18. Grigg, R.; Sridharan, V. J. Organomet. Chem. 1999, 576, 65
19. Miura, T.; Murakami, M. Chem. Commun. 2007, 217
20. Malacria, M. Chem. Rev. 1996, 96, 289
21. Nicolaou, K. C.; Montagnon, T.; Snyder, S. A. Chem. Commun. 2003, 551
22. Nicolaou, K. C.; Edmonds, D. J.; Bulger, P. G. Angew. Chem., Int. Ed. 2006, 45, 7134
23. Enders, D.; Grondal, C.; Hüttl, M. R. M. Angew. Chem., Int. Ed. 2007, 46, 1570
24. Tietze, L. F.; Brasche, G.; Gericke, K. Domino Reactions in Organic Synthesis; Wiley-VCH: Weinheim, 2006.
25. Tietze, L. F.; Düfert, M. A.; Hungerland, T.; Oum, K.; Lenzer, T. Chem.-Eur. J. 2011, 17, 8452
26. Ren, H.; Luo, Y.; Ye, S.; Wu, J. Org. Lett. 2011, 13, 2552
27. Ye, S.; Wang, H.; Wu, J. ACS Comb. Sci. 2011, 13, 120
28. Zheng, D.; Chen, Z.; Liu, J.; Wu, J. Org. Biomol. Chem. 2011, 9, 4763
29. Ye, S.; Wang, H.; Wu, J. Tetrahedron 2011, 67, 4628
30. Zheng, D.; Wang, Z.; Wu, J. Synthesis 2011, 2810
31. Ye, S.; Gao, K.; Wu, J. Adv. Synth. Catal. 2010, 352, 1746
32. Ye, S.; Wang, H.; Wu, J. Eur. J. Org. Chem. 2010, 6436
33. Chen, Z.; Yu, X.; Su, M.; Yang, X.; Wu, J. Adv. Synth. Catal. 2009, 351, 2702
34. Ding, Q.; Wang, Z.; Wu, J. J. Org. Chem. 2009, 74, 921
35. Ding, Q.; Wu, J. Adv. Synth. Catal. 2008, 350, 1850
36. Yeom, H.-S.; Kim, S.; Shin, S. Synlett 2008, 924
37. Huo, Z.; Tomeba, H.; Yamamoto, Y. Tetrahedron Lett. 2008, 49, 5531
38. Nakamuran, I.; Yamamoto, Y. Adv. Synth. Catal. 2002, 344, 111
39. Brandi, A.; Cicchi, S.; Cordero, F. M.; Goti, A. Chem. Rev. 2003, 103, 1213
40. Nakamura, E.; Yamago, S. Acc. Chem. Res. 2002, 35, 867
41. Shao, L.-X.; Shi, M. Curr. Org. Chem. 2007, 11, 1135
42. Rubin, M.; Rubina, M.; Gevorgyan, V. Chem. Rev. 2007, 107, 3117
43. Hu, B.; Xing, S. Y.; Wang, Z. W. Org. Lett. 2008, 10, 5481
44. Huang, X.; Yang, Y. Org. Lett. 2007, 9, 1667
45. Lautens, M.; Han, W. J. Am. Chem. Soc. 2002, 124, 6312
46. Lautens, M.; Han, W.; Liu, J. H. J. Am. Chem. Soc. 2003, 125, 4028
47. Scott, M. E.; Bethuel, Y.; Lautens, M. J. Am. Chem. Soc. 2007, 129, 1482
48. Scott, M. E.; Schwarz, C. A.; Lautens, M. Org. Lett. 2006, 8, 5521
49. Scott, M. E.; Han, W.; Lautens, M. Org. Lett. 2004, 6, 3309
50. Scott, M. E.; Lautens, M. Org. Lett. 2005, 7, 3045
51. Yu, L.; Meng, J. D.; Xia, L.; Guo, R. J. Org. Chem. 2009, 74, 5087
52. Lu, L.; Chen, G.; Ma, S. Org. Lett. 2006, 8, 835
53. Scott, M. E.; Lautens, M. J. Org. Chem. 2008, 73, 8154
54. Taillier, C.; Lautens, M. Org. Lett. 2007, 9, 591
55. Diev, V. V.; Tung, T. Q.; Molchanov, A. P. Eur. J. Org. Chem. 2009, 525
56. Hu, B.; Zhu, J. L.; Xing, S. Y.; Fang, J.; Du, D.; Wang, Z. W. Chem.-Eur. J. 2009, 15, 324
57. Bagutski, V.; de Meijere, A. Adv. Synth. Catal. 2007, 349, 1247
58. Hang, X.-C.; Chen, Q.-Y.; Xiao, J.-C. Eur. J. Org. Chem. 2008, 1101
59. Shi, M.; Xu, B.; Huang, J.-W. Org. Lett. 2004, 6, 1175
60. Shi, M.; Liu, L.-P.; Tang, J. Org. Lett. 2006, 8, 4043
61. Yao, L.-F.; Shi, M. Eur. J. Org. Chem. 2009, 4971
62. Jiang, M.; Liu, L.-P.; Shi, M.; Li, Y.-X. Org. Lett. 2010, 12, 116
63. Jiang, M.; Shi, M. Org. Lett. 2010, 12, 2606
64. Huang, X.; Miao, M.-Z. J. Org. Chem. 2008, 73, 6884
65. Tang, X.-Y.; Wei, Y.; Shi, M. Org. Lett. 2010, 12, 5120
66. Hubert, C.; Moreau, J.; Batany, J.; Duboc, A.; Hurvois, J.-P.; Renaud, J. L. Adv. Synth. Catal. 2008, 350, 40
67. Moreau, J.; Hubert, C.; Batany, J.; Toupet, L.; Roisnel, T.; Hurvois, J.-P.; Renaud, J.-L. J. Org. Chem. 2009, 74, 8963
68. Ma, S.; Lu, L. J. Org. Chem. 2005, 70, 7629
69. Coskun, N.; Tuncman, S. Tetrahedron 2006, 62, 1345
70. Ding, Q.; Wang, Z.; Wu, J. J. Org. Chem. 2009, 74, 921