Catalytic asymmetric allylic alkylation of 3-arylated piperidin-2-ones

European Journal of Organic Chemistry

Volumn , Issue 22, 2013, Pages 4979-4985

  Michon, Christophe ^a,b,c   Béthegnies, Aurélien ^a,b,c   Capet, Frédéric ^a,b,c   Roussel, Pascal ^a,b,c   De Filippis, Arnault ^d   Gomez Pardo, Domingo ^d   Cossy, Janine ^d   Agbossou Niedercorn, Francine ^a,b,c  

^a UNIV LILLE   (France)

^b UNITÉ DE CATALYSE ET DE CHIMIE DU SOLIDE   (France)

^c Ecole Nationale Superieure de Chimie de Lille   (France)

^d CNRS   (France)

Author keywords

Alkylation; Asymmetric catalysis; Heterocycles; Lactams; Palladium

Indexed keywords

EID: 84880938222     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.201300510     Document Type: Article

References (68)

1. D. Regoli, A. Bourdon, J. L. Fauchere, Pharmacol. Rev. 1994, 46, 551-599.
2. J. N. Pennefather, A. Lecci, M. L. Candenas, E. Patak, F. M. Pinto, C. A. Maggi, Life Sci. 2004, 74, 1445-1463.
3. N. M. J. Rupniak, M. S. Kramer, Trends Pharmacol. Sci. 1999, 20, 485-490.
4. C. Severini, G. Improta, G. Falconieri-Erspamer, S. Salvadori, V. Erspamer, Pharmacol. Rev. 2002, 54, 285-322.
5. A. Lecci, A. Capriati, C. A. Maggi, Br. J. Pharmacol. 2004, 141, 1249-1263.
6. M. Bayés, X. Rabasseda, J. R. Prous, Methods Find. Exp. Clin. Pharmacol. 2004, 26, 129-161.
7. M. Grugni, R. Rigolio, K. F. Erhard, WO 9805640 A2, 1998
8. [Chem. Abstr. 1995, 128, 167355]
9. G. A. M. Giardina, M. Grugni, R. Rigolio, M. Vassallo, K. Erhard, C. Farina, Bioorg. Med. Chem. Lett. 1996, 6, 2307-2310.
10. H. G. Chen, F. Z. Chung, O. P. Goel, D. Johnson, S. Kesten, J. Knobelsdorf, H. T. Lee, J. R. Rubin, Bioorg. Med. Chem. Lett. 1997, 7, 555-560.
11. A. Alcade, G. Anne-Archard, D. Capraro, WO 03008382 A1, 2003
12. [Chem. Abstr. 2003, 138, 137171]
13. B. Castro, J. R. Dormoy, A. Rabion, WO 0037445 A1, 2000
14. [Chem. Abstr. 2000, 133, 73938]
15. P. Camus, M. Descamps, J. Radisson, WO 9732852 A1, 1997
16. [Chem. Abstr. 1997, 127, 278145]
17. P. Goulaouic, X. Emonds-Alt, P. Gueule, V. Proietto, EP 512901 A1, 1992
18. [Chem. Abstr. 1992, 118, 124405k]
19. D. Bichon, D. Van Broeck, V. Proietto, P. Gueule, X. Emonds-Alt, EP 673928 A1, 1995
20. [Chem. Abstr. 1995, 124, 117093c];.
21. S. B. Sobolov-Jaynes, J. A. Lowe III, S. Mclean, WO 2004000355, 2003
22. [Chem. Abstr. 2004, 140, 71043]
23. J. A. Lowe III, EP 1192952A2, 2002
24. [Chem. Abstr. 2002, 136, 273215];.
25. T. P. Burkholder, L. D. Bratton, E. M. Kudlacz, G. P. Maynard, J. M. Kane, B. Santiago, US 6329392B1, 2001
26. [Chem. Abstr. 2001, 136, 20072]
27. A. Poulsen, T. Liljefors, K. Gundertofte, B. Bjornholm, J. Comput.-Aided Mol. Des. 2002, 16, 273-286.
28. T. X. Métro, A. Cochi, D. Gomez-Pardo, J. Cossy, J. Org. Chem. 2011, 76, 2594-2602.
29. J. Keldenich, C. Michon, A. Nowicki, F. Agbossou-Niedercorn, Synlett 2011, 2939-2942.
30. A. Cochi, T. X. Métro, D. Gomez-Pardo, J. Cossy, Org. Lett. 2010, 12, 3693-3695.
31. A. Nowicki, J. Keldenich, F. Agbossou-Niedercorn, Eur. J. Org. Chem. 2007, 6124-6127.
32. A. Nowicki, A. Mortreux, F. Agbossou-Niedercorn, Tetrahedron Lett. 2005, 46, 1617-1621.
33. A. Nowicki, A. Mortreux, F. Agbossou-Niedercorn, Tetrahedron: Asymmetry 2005, 16, 1295-1298.
34. J. Fournier, O. Lozano, C. Menozzi, S. Arseniyadis, J. Cossy, Angew. Chem. 2013, 125, 1295-1299; Angew. Chem. Int. Ed. 2013, 52, 1257 -1261.
35. B. M. Trost, Org. Process Res. Dev. 2012, 16, 185-194.
36. B. M. Trost, B. Schäffner, M. Osipov, D. A. A. Wilton, Angew. Chem. 2011, 123, 3610-3613; Angew. Chem. Int. Ed. 2011, 50, 3548 -3551.
37. I. Guerrero Rios, A. Rosas-Hernandez, E. Martin, Molecules 2011, 16, 970-1010.
38. B. M. Trost, L. C. Czabaniuk, J. Am. Chem. Soc. 2010, 132, 15534-15536.
39. Z. Lu, S. Ma, Angew. Chem. 2008, 120, 264-303; Angew. Chem. Int. Ed. 2008, 47, 258 -297.
40. N. B. Bennett, D. C. Duquette, J. Kim, W. B. Liu, A. N. Marziale, D. C. Behenna, S. C. Virgil, B. M. Stoltz, Chem. Eur. J. 2013, 19, 4414-4418.
41. D. C. Behenna, Y. Liu, T. Yurino, J. Kim, D. E. White, S. C. Virgil, B. M. Stoltz, Nature Chem. 2012, 4, 130-133.
42. L. Li, W. Chen, W. Yang, Y. Pan, H. Liu, C. H. Tan, Z. Jiang, Chem. Commun. 2012, 48, 5124-5126.
43. Y. Park, Y. J. Lee, S. Hong, M. H. Kim, M. Lee, T. S. Kim, J. K. Lee, S. S. Jew, H. G. Park, Adv. Synth. Catal. 2011, 353, 3313-3318.
44. T. A. Moss, B. Alonso, D. R. Fenwick, D. J. Dixon, Angew. Chem. 2010, 122, 578-581; Angew. Chem. Int. Ed. 2010, 49, 568 -571.
45. M. E. Muratore, C. A. Holloway, A. W. Pilling, R. I. Storer, G. Trevitt, D. J. Dixon, J. Am. Chem. Soc. 2009, 131, 10796-10797.
46. S. Ma, X. Han, S. Krishnan, S. C. Virgil, B. M. Stoltz, Angew. Chem. 2009, 121, 8181-8185; Angew. Chem. Int. Ed. 2009, 48, 8037 -8041.
47. S. A. Shaw, P. Aleman, J. Christy, J. W. Kampf, P. Va, E. Vedejs, J. Am. Chem. Soc. 2006, 128, 925-934.
48. A. P. Degnan, A. I. Meyers, J. Am. Chem. Soc. 1999, 121, 2762-2769.
49. M. Amat, M. Pérez, J. Bosch, Synlett 2011, 143-160.
50. Y. Zhao, Y. Zhou, L. Liang, X. Yang, F. Du, L. Li, H. Zhang, Org. Lett. 2009, 11, 555-558.
51. B. M. Trost, J. Quancard, J. Am. Chem. Soc. 2006, 128, 6314-6315.
52. B. M. Trost, M. K. Brennan, Org. Lett. 2006, 8, 2027-2030.
53. B. M. Trost, W. Tang, J. Am. Chem. Soc. 2003, 125, 8744-8745.
54. J. Cossy, A. de Filippis, D. Gomez-Pardo, Org. Lett. 2003, 5, 3037-3039.
55. J. Cossy, A. de Filippis, D. Gomez-Pardo, Synlett 2003, 2171-2174.
56. A. de Filippis, D. Gomez-Pardo, J. Cossy, Tetrahedron 2004, 60, 9757-9767.
57. A. de Filippis, D. Gomez-Pardo, J. Cossy, Synthesis 2004, 2930-2933.
58. L. A. Evans, N. Fey, J. N. Harvey, D. Hose, G. C. Lloyd-Jones, P. Murray, A. G. Orpen, R. Osborne, G. J. J. Owen-Smith, M. Purdie, J. Am. Chem. Soc. 2008, 130, 14471-14473.
59. G. Helmchen, A. Pfaltz, Acc. Chem. Res. 2000, 33, 336-345.
60. M. Diéguez, O. Pamies, Acc. Chem. Res. 2010, 43, 312-322.
61. G. Helmchen, A. Dahnz, P. Dübon, M. Schelwies, R. Weihofen, Chem. Commun. 2007, 675-691.
62. J. F. Hartwig, L. M. Stanley, Acc. Chem. Res. 2010, 43, 1461-1475.
63. R. Takeuchi, S. Kezuka, Synthesis 2006, 3349-3366.
64. H. Miyabe, Y. Takemoto, Synlett 2005, 1641-1655.
65. R. Yanada, N. Negoro, K. Bessho, K. Yanada, Synlett 1995, 1261-1263.
66. CCDC-932181 (for 8) and -CCDC-932180 (for 12) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data- request/cif.
67. A. E. Sorochinsky, J. L. Aceña, V. A. Soloshonok, Synthesis 2013, 45, 141-152.
68. V. A. Soloshonok, C. Roussel, O. Kitagawa, A. E. Sorochinsky, Chem. Soc. Rev. 2012, 41, 4180-4188.