Enantioselective zirconium-catalyzed friedel-crafts alkylation of pyrrole with trifluoromethyl ketones

Organic Letters

Volumn 11, Issue 2, 2009, Pages 441-444

  Blay, Gonzalo ^a   Fernández, Isabel ^a   Monleón, Alicia ^a   Pedro, José R ^a   Vila, Carlos ^a  

^a UNIVERSITY OF VALENCIA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

KETONE; PYRROLE DERIVATIVE; ZIRCONIUM;

ALKYLATION; ARTICLE; CATALYSIS; CHEMISTRY; ENZYME SPECIFICITY; STEREOISOMERISM;

ALKYLATION; CATALYSIS; KETONES; PYRROLES; STEREOISOMERISM; SUBSTRATE SPECIFICITY; ZIRCONIUM;

EID: 61449178929     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol802509m     Document Type: Article

References (57)

1. (a) Organofluorine Compounds: Chemistry Applications; Hiyama, T., Ed.; Springer: New York, 2000.
2. (b) Kirsch, P. Modern Fluoroorganic Chemistry; Wiley-VCH: Weinheim, Germany, 2004.
3. (c) Chambers, R. D. Fluorine in Organic Chemistry; Blackwell: Oxford, U.K., 2004.
4. (d) Shah, P. A.; Westwell, D. J. Enzyme Inhib. Med. Chem. 2007, 22, 527-540.
5. (e) Müller, K.; Faeh, C.; Diederich, F. Science 2007, 317, 1881-1886.
6. (f) Kirk, K. L. Org. Process Res. Dev. 2008, 12, 305-321.
7. (g) Purser, S.; Moore, P. R.; Swallow, S.; Gouverneur, V. Chem. Soc. Rev. 2008, 37, 320-330.
8. (h) Zhu, Y.; Zhao, P.; Cai, X.; Meng, W.-D.; Qing, F.-L. Polymer 2007, 48, 3116-3124.
9. (i) Tsuchiya, K.; Shibasaki, Y.; Aoyagi, M.; Ueda, M. Macromolecules 2006, 39, 3964-3966.
10. (a) Quaternary Stereocenters: Challenges and Solutions for Organic Synthesis; Christoffers, J. C., Baro, A., Eds.; Wiley-VCH: Weinheim: Germany, 2006.
11. (b) Christoffeis, J.; Mann, A. Angew. Chem., Int. Ed. 2001, 40, 4591-4597.
12. (c) Ramon, D. J.; Yus, M. Curr. Org. Chem. 2004, 8, 149-183.
13. (d) Mikami, K.; Itoh, Y.; Yamanaka, M. Chem. Rev. 2004, 104, 1-16.
14. (e) Christoffers, J.; Baro, A. Adv. Synth. Catal. 2005, 347, 1473-1482.
15. (f) Trost, B. M.; Jiang, C. H. Synthesis 2006, 369-396.
16. (g) Riant, O.; Hannedouche, J. Org. Biomol. Chem. 2007, 5, 873-888.
17. (h) Cozzi, P. G.; Hilgraf, R.; Zimmermann, N. Eur. J. Org. Chem. 2007, 5969-5994.
18. (a) Grabowski, E. J. J. Chirality 2005, 17, S249-S259.
19. (b) Pierce, M. E.; Parsons, R. L., Jr.; Radesca, L. A.; Lo, Y. S.; Silverman, S.; Moore, J. R.; Islam, Q.; Choudhury, A.; Fortunak, J. M. D.; Nguyen, D.; Luo, C.; Morgan, S. J.; Davis, W. P.; Confalone, P. M.; Chen, C.-Y.; Tillyer, R. D.; Frey, L.; Tan, L.; Xu, F.; Zhao, D.; Thompson, A. S.; Corley, E. G. J. Org. Chem. 1998, 63, 8536-8543.
20. Caron, S.; Do, N. M.; Sieser, J. E.; Arpin, P.; Vazquez, E. Org. Process Res. Dev. 2007, 11, 1015-1024.
21. (a) Chang, Y.; Cai, C. Tetrahedron Lett. 2005, 46, 3161-3164.
22. (b) Roussel, S.; Billard, T.; Langlois, B. R.; Saint-James, L. Chem. Eur. J. 2005, 11, 939-944.
23. (c) Prakash, G. K. S.; Hu, J.; Olah, G. A. J. Org. Chem. 2003, 68, 4457-4463.
24. (d) Langlois, B. R.; Billard, T. Synthesis 2003, 185-194.
25. (e) Joubert, J.; Roussel, S.; Christophe, C.; Billard, T.; Langlois, B. R.; Vidal, T. Angew. Chem., Int. Ed. 2003, 42, 3133-3136.
26. (f) Prakash, G. K. S.; Hu, J.; Olah, G. A. Org. Lett. 2003, 5, 3253-3256.
27. (g) Roussel, S.; Billard, T.; Langlois, B. R.; Saint-James, L. Synthesis 2004, 2119-2122.
28. (a) Langlois, B. R.; Billard, T.; Roussel, S. J. Fluorine Chem. 2005, 126, 173-179.
29. (b) Ma, J.-A.; Canard, D. Chem. Rev. 2004, 104, 6119-6146.
30. (a) Ramón, D. J.; Yus, M. Angew. Chem., Int. Ed. 2004, 43, 284-287.
31. (b) Li, H.; Walsh, P. J. J. Am. Chem. Soc. 2005, 127, 8355-8361.
32. (c) Jeon, S.-J.; Li, H.; Walsh, P. J. J. Am. Chem. Soc. 2005, 127, 16416-16425.
33. (d) Cozzi, P. G.; Rudolph, J.; Bolm, C.; Norrby, P.-O.; Tomassini, C. J. Org. Chem. 2005, 70, 5733-5736.
34. (e) Ni, M.; Wang, R.; Han, Z.-J.; Mao, B.; Da, C.-S.; Liu, L.; Chen, C. Adv. Synth. Catal. 2005, 347, 1659-1665.
35. (f) Jeon, S.-J.; Li, H.; García, C.; LaRochelle, L. K.; Walsh, P. J. J. Org. Chem. 2005, 70, 448-455.
36. (g) Cozzi, P. G. Angew. Chem., Int. Ed. 2003, 42, 2895-2898.
37. (h) García, C.; Walsh, P. J. Org. Lett. 2003, 5, 3641-3644.
38. (i) Tomita, D.; Wada, R.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2005, 127, 4138-4139.
39. Martina, S. L. X.; Jagt, R. B. C.; de Vries, J. G.; Feringa, B. L.; Minnaard, A. J. Chem. Commun. 2006, 4093-4095.
40. (a) Tur, F.; Saá, J. M. Org. Lett. 2007, 9, 5079-5082.
41. (b) Bandini, M.; Sinisi, R.; Umani-Ronchi, A. Chem. Commun. 2008, 4360-4362.
42. (a) Zhuang, W.; Gatherhood, N.; Hazell, R. G.; Jørgensen, K. A. J. Org. Chem. 2001, 66, 1009-1013.
43. (b) Lyle, M. P. A.; Draper, N. D.; Wilson, P. D. Org. Lett. 2005, 7, 901-904.
44. (c) Török, B.; Abid, M.; London, G.; Esquibel, J.; Török, M.; Mhadgut, S. C.; Yand, P.; Prakash, G. K. S. Angew. Chem., Int. Ed. 2005, 44, 3086-3089.
45. (a) Shibasaki, M.; Matsunaga, S. Chem. Soc. Rev. 2006, 35, 269-279.
46. (b) Brunel, J. M. Chem. Rev. 2005, 105, 857-898.
47. (c) Shibasaki, M.; Yoshikawa, N. Chem. Rev. 2002, 102, 2187-2210.
48. (d) Saruhashi, K.; Shibashaki, S. J. Am. Chem. Soc. 2006, 128, 11232-11235.
49. (e) Ihori, Y.; Yamashita, I.; Ishitani, H.; Kobayashi, H. J. Am. Chem. Soc. 2005, 127, 15528-15532.
50. (f) Kobayashi, S.; Kobayashi, J.; Ishani, H.; Ueno, M. Chem. Eur. J. 2002, 8, 4185-4190.
51. Blay, G.; Fernández, I.; Pedro, J. R.; Vila, C. Org. Lett. 2007, 9, 2601-2604.
52. Trost, B. M.; Müller, C. J. Am. Chem. Soc. 2008, 130, 2438-2439.
53. (a) Çavdar, H.; Saraçoglu, N. Tetrahedron 2005, 61, 2401-2405.
54. (b) Evans, D. A.; Fandrick, K. R. Org. Lett. 2006, 8, 2249-2252.
55. (c) Blay, G.; Fernández, I.; Pedro, J. R.; Vila, C. Tetrahedron Lett. 2007, 48, 6731-6734.
56. Ohta, H.; Miyamae, Y.; Kimura, Y. Chem. Lett. 1989, 379-380.
57. Kohler, F.; Gais, H.-J.; Raabe, G. Org. Lett. 2007, 9, 1231-1234.