Expedient synthesis of highly substituted pyrroles via tandem rearrangement of α-diazo oxime ethers

Journal of the American Chemical Society

Volumn 134, Issue 9, 2012, Pages 4104-4107

  Jiang, Yaojia ^a   Chan, Wei Chuen ^a   Park, Cheol Min ^a  

^a Nanyang Technological University   (Singapore)

Author keywords

[No Author keywords available]

Indexed keywords

2H-AZIRINES; OXIME ETHERS; QUATERNARY CENTERS; RHODIUM-CATALYZED SYNTHESIS;

ETHERS; POSITIVE IONS; RHODIUM;

ORGANIC COMPOUNDS;

2H AZIRINE; ALPHA DIAZO OXIME ETHER; AZIRINE DERIVATIVE; ETHER DERIVATIVE; PYRROLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ATOM; CHEMICAL REACTION; CYCLOADDITION; PHOTOCHEMISTRY; SYNTHESIS;

AZO COMPOUNDS; ETHERS; MOLECULAR STRUCTURE; OXIMES; PYRROLES; STEREOISOMERISM;

EID: 84863229529     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja300552c     Document Type: Article

References (58)

1. Comprehensive Heterocyclic Chemistry II; Fan, W. Q.; Katritzky, A. R.; Rees, C. W.; Scriven, E. F. V., Eds.; Pergamon Press: Oxford, 1996; Vol. 2.
2. (a) Fan, H.; Peng, J.; Hamann, M. T.; Hu, J.-F. Chem. Rev. 2007, 108, 264.
3. (b) Grube, A.; Köck, M. Org. Lett. 2006, 8, 4675.
4. (c) Fujita, M.; Nakao, Y.; Matsunaga, S.; Seiki, M.; Itoh, Y.; Yamashita, J.; van Soest, R. W. M.; Fusetani, N. J. Am. Chem. Soc. 2003, 125, 15700.
5. (d) Fürstner, A. Angew. Chem., Int. Ed. 2003, 42, 3582.
6. (e) Boger, D. L.; Boyce, C. W.; Labroli, M. A.; Sehon, C. A.; Jin, Q. J. Am. Chem. Soc. 1999, 121, 54.
7. Lohray, B. B.; Lohray, V. Pure Appl. Chem. 2005, 77, 179.
8. (a) Berlin, A.; Vercelli, B.; Zotti, G. Polym. Rev. (Philadelphia, PA, U.S.) 2008, 48, 493.
9. (b) Gabriel, S.; Cécius, M.; Fleury-Frenette, K.; Cossement, D.; Hecq, M.; Ruth, N.; Jérôme, R.; Jérôme, C. Chem. Mater. 2007, 19, 2364.
10. (c) Novák, P.; Müller, K.; Santhanam, K. S. V.; Haas, O. Chem. Rev. 1997, 97, 207.
11. (a) Padwa, A.; Pearson, W. H. Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry toward Heterocycles and Natural Products; Wiley: New York, 2002; Vol. 59.
12. (b) St. Cyr, D. J.; Arndtsen, B. A. J. Am. Chem. Soc. 2007, 129, 12366.
13. (a) Estevez, V.; Villacampa, M.; Menendez, J. C. Chem. Soc. Rev. 2010, 39, 4402.
14. (b) Balme, G. Angew. Chem., Int. Ed. 2004, 43, 6238.
15. (c) Fontaine, P.; Masson, G. r.; Zhu, J. Org. Lett. 2009, 11, 1555.
16. (d) Bharadwaj, A. R.; Scheidt, K. A. Org. Lett. 2004, 6, 2465.
17. (e) Dhawan, R.; Arndtsen, B. A. J. Am. Chem. Soc. 2003, 126, 468.
18. (a) Rakshit, S.; Patureau, F. W.; Glorius, F. J. Am. Chem. Soc. 2010, 132, 9585.
19. (b) Huestis, M. P.; Chan, L.; Stuart, D. R.; Fagnou, K. Angew. Chem., Int. Ed. 2011, 50, 1338.
20. (c) Mizuno, A.; Kusama, H.; Iwasawa, N. Angew. Chem., Int. Ed. 2009, 48, 8318.
21. Padwa, A.; Smolanoff, J.; Tremper, A. J. Am. Chem. Soc. 1975, 97, 4682.
22. (a) Skepper, C. K.; Molinski, T. F. J. Org. Chem. 2008, 73, 2592.
23. (b) Salomon, C. E.; Williams, D. H.; Faulkner, D. J. J. Nat. Prod. 1995, 58, 1463.
24. (c) Molinski, T. F.; Ireland, C. M. J. Org. Chem. 1988, 53, 2103.
25. (a) Padwa, A. In Advances in Heterocyclic Chemistry; Katritzky, A. R., Ed.; Academic Press: Orlando, FL, 2010; Vol. 99, p 1.
26. (b) Gilchrist, T. L.; Alves, M. J. In Organic Azides; John Wiley & Sons Ltd.: Chichester, U.K., 2010; p 167.
27. (c) Palacios, F.; de Retana, A. M. O.; de Marigorta, E. M.; de los Santos, J. M. Eur. J. Org. Chem. 2001, 2001, 2401.
28. (d) Palacios, F.; de Retana, A. M. O.; de Marigorta, E. M.; Santos, J. M. d. l. Org. Prep. Proced. Int. 2002, 34, 219.
29. (e) Singh, G. S.; D'Hooghe, M.; De Kimpe, N. Chem. Rev. 2007, 107, 2080.
30. (f) e Melo, T. M. V. D. P.; Amd'Ar, G. Curr. Org. Synth. 2004, 1, 275.
31. (a) Jana, S.; Clements, M. D.; Sharp, B. K.; Zheng, N. Org. Lett. 2010, 12, 3736.
32. (b) Candito, D. A.; Lautens, M. Org. Lett. 2010, 12, 3312.
33. (c) Padwa, A.; Stengel, T. Tetrahedron Lett. 2004, 45, 5991.
34. (d) Johns, B. A.; Gudmundsson, K. S.; Turner, E. M.; Allen, S. H.; Jung, D. K.; Sexton, C. J.; Boyd, F. L. Jr.; Peel, M. R. Tetrahedron 2003, 59, 9001.
35. (e) Stevens, K. L.; Jung, D. K.; Alberti, M. J.; Badiang, J. G.; Peckham, G. E.; Veal, J. M.; Cheung, M.; Harris, P. A.; Chamberlain, S. D.; Peel, M. R. Org. Lett. 2005, 7, 4753.
36. (f) Brahma, S.; Ray, J. K. J. Heterocycl. Chem. 2008, 45, 311.
37. (g) Alves, M. J.; Gil Fortes, A.; Lemos, A.; Martins, C. Synthesis 2005, 2005, 555.
38. (h) Timen, A. S.; Fischer, A.; Somfai, P. Chem. Commun. 2003, 1150.
39. (i) Taber, D. F.; Tian, W. J. Am. Chem. Soc. 2006, 128, 1058.
40. Rappoport, Z.; Liebman, J. F. The Chemistry of Hydroxylamines, Oximes and Hydroxamic Acids; Wiley: Hoboken, NJ, 2008; Vol. 2.
41. (a) Banert, K. In Organic Azides; John Wiley & Sons, Ltd: Chichester, U.K., 2010; p 113.
42. (b) Sjöholm Timén, Å.; Risberg, E.; Somfai, P. Tetrahedron Lett. 2003, 44, 5339.
43. (a) Kirmse, W. Eur. J. Org. Chem. 2002, 2002, 2193.
44. (b) Tidwell, T. T. Angew. Chem., Int. Ed. 2005, 44, 5778.
45. (a) Seki, H.; Georg, G. I. J. Am. Chem. Soc. 2010, 132, 15512.
46. (b) Presset, M.; Coquerel, Y.; Rodriguez, J. J. Org. Chem. 2008, 74, 415.
47. (c) Sarpong, R.; Su, J. T.; Stoltz, B. M. J. Am. Chem. Soc. 2003, 125, 13624.
48. (d) Dalton, A. M.; Zhang, Y.; Davie, C. P.; Danheiser, R. L. Org. Lett. 2002, 4, 2465.
49. (e) de Lucas, N. C.; Netto-Ferreira, J. C.; Andraos, J.; Scaiano, J. C. J. Org. Chem. 2001, 66, 5016.
50. Lourdusamy, E.; Yao, L.; Park, C.-M. Angew. Chem., Int. Ed. 2010, 49, 7963.
51. Preparation of α-diazo β-keto oxime ethers. For details, see ref 16 and the Supporting Information. (Chemical Equation Presented)
52. (a) Manning, J. R.; Davies, H. M. L. J. Am. Chem. Soc. 2008, 130, 8602.
53. (b) Manning, J. R.; Davies, H. M. L. Tetrahedron 2008, 64, 6901.
54. (a) P. Marsden, S.; Pang, W.-K. Chem. Commun. 1999, 1199.
55. (b) Collomb, D.; Doutheau, A. Tetrahedron Lett. 1997, 38, 1397.
56. (c) Karady, S.; Amato, J. S.; Reamer, R. A.; Weinstock, L. M. Tetrahedron Lett. 1996, 37, 8277.
57. Qi, X.; Jiang, Y.; Park, C.-M. Chem. Commun. 2011, 47, 7848.
58. Plausible mechanism for the formation of 2k". (Chemical Equation Presented)