The synthesis of polysubstituted pyrroles via the coupling of phenyliodonium ylides and enamine esters

Advanced Synthesis and Catalysis

Volumn 351, Issue 13, 2009, Pages 2063-2066

  Wang, Jun Yan ^a   Wang, Xian Pei ^a   Yu, Zheng Sen ^a   Yu, Wei ^a  

^a LANZHOU UNIVERSITY   (China)

Author keywords

Coupling reactions; Enamine esters; Phenyliodonium ylides; Pyrroles

Indexed keywords

EID: 70349419649     PISSN: 16154150     EISSN: 15213897     Source Type: Journal    
DOI: 10.1002/adsc.200900379     Document Type: Article

References (38)

1. A. Fürstner, Angew. Chem. 2003, 775, 3706;
2. Angew. Chem. Int. Ed. 2003, 42, 3582.
3. a) J. W. Huffman, Curr. Med. Chem. 1999, 6, 705;
4. b) S. Agarwal, S. Cämmerer, S. Filali, W. Fröhner, J. Knöll, M. P. Krahl, K. R. Reddy, H.J. Knölker, Curr. Org. Chem. 2005, 9, 1601.
5. V. M. Domingo, C. Alemán, E. Brillas, L. Julia, J. Org. Chem. 2001, 66, 4058.
6. a) T. L. Gilchrist, J. Chem. Soc. Perkin Trans 1 2001, 2491;
7. b)G. Balme, Angew. Chem. 2004, 776, 6396;
8. Angew. Chem. Int. Ed. 2004, 43, 6238.
9. For some recent examples of pyrrole synthesis, see: a) S. Su, J. A. Porco Jr, J. Am. Chem. Soc. 2007, 729, 7744;
10. b) D. J. St. Cyr, N. Martin, B. A. Arndtsen, Org. Lett. 2007, 9, 449;
11. c)M. R. Rivero, S. L. Buchwald, Org. Lett. 2007, 9, 973;
12. d) L. Peng, X. Zhang, J. Ma, Z. Zhong, J. Wang, Org. Lett. 2007, 9, 1445;
13. e)F.M. Is-trate, F. Gagosz, Org. Lett. 2007, 9, 3181;
14. f) S. Chiba, Y.-F. Wang, ; G. Lapointe, K. Narasaka, Org. Lett. 2008, 10, 313;
15. g) O. A. Attanasi, G. Favi, P. Filippone, G. Giorgi, F. Mantellina, G. Moscatelli, D. Spinelli, Org. Lett. 2008, 10, 1983;
16. h) S. Cacchi, G. Fabrizi, E. Filisti, Org. Lett. 2008, 10, 2629;
17. i) Y.-F. Wang, Toh, K. K. S. Chiba, K. Narasaka, Org. Lett. 2008, 10, 5019;
18. j) X. Liu, L. Huang, F. Zheng, Z. Zhan, Adv. Synth. Catal. 2008, 350, 2778;
19. k) F. A. Davis, V. A. Bowen, H. Xu, V. Velvadapu, Tetrahedron 2008, 64, 4174;
20. l)M. J. R. P. Queiroz, A. Begouin, G Pereira, P. M. T. Ferreira, Tetrahedron 2008, 64, 10714;
21. m) B. Alcaide, P. Almendros, R. Carrascosa, M. C. Redondo, Chem. Eur. J. 2008, 14, 637;
22. n)B. Tan, Z. Shi, P.J. Chua, Y. Li, G. Zhong, Angew. Chem. Int. Ed. 2009, 48, 758;
23. o) A. V. Lygin, O. V. Larionov, V. S. Korotkov, A. de Meijere, Chem. Eur. J. 2009, 15, 227;
24. p) D. Tejedor, S. Lõpez-Tosco, J. Gozález-Platas, F. Garcia-Tellado, Chem. Eur. J. 2009, 15, 838;
25. q) Y. Kim, J. Kim, S. B. Park, Org. Lett. 2009, 77, 17;
26. r) Y. Lu, X. Fu, H. Chen, X. Du, X. Jia, Y. Liu, Adv. Synth. Catal. 2009, 357, 129.
27. a) V. V. Zhdankin, P.J. Stang, Chem. Rev. 2002, 102, 2523;
28. b)V.V. Zhdankin, P.J. Stang, Chem. Rev. 2008, 108, 5299;
29. c)X.-C. Huang, Y.-L. Liu, Y. Liang, S.-F. Pi, F. Wang, J.-H. Li, Org. Lett. 2008, 10, 1525.
30. For reviews, see: a) P. Müller, Ace. Chem. Res 2004, 37, 243;
31. b) R. M. Moriarty, J. Org. Chem. 2005, 70, 2853;
32. for several recent examples: c) P. Müller, Y Allenbach, E. Robert, Tetrahedron: Asymmetry 2003, 14, 779;
33. d)B. Moreau, A.B. Charette, J. Am. Chem. Soc. 2005, 727, 18014.
34. S. Telu, S. Durmus, G F. Koser, Tetrahedron Lett. 2007, 48, 1863.
35. K. Schank, G Lick, Synthesis 1983, 392.
36. a) Z.-H. Zhang, L. Yin, Y.-M. Wang, Adv. Synth. Catal. 2006, 348, 184;
37. b) W Tang, W. Wang, Y. Chi, X. Zhang, Angew. Chem. 2003, 775, 3633;
38. Angew. Chem. Int. Ed. 2003, 42, 3509.