Copper/palladium-catalyzed 1,4 reduction and asymmetric allylic alkylation of α,β-unsaturated ketones: Enantioselective dual catalysis

Angewandte Chemie - International Edition

Volumn 52, Issue 11, 2013, Pages 3208-3212

  Nahra, Fady ^a   Macé, Yohan ^a   Lambin, Dominique ^a   Riant, Olivier ^a  

^a UNIVERSITÉ CATHOLIQUE DE LOUVAIN   (Belgium)

Author keywords

asymmetric allylic alkylation; copper; dual catalysis; Michael acceptors; palladium

Indexed keywords

ASYMMETRIC ALLYLIC ALKYLATIONS; CATALYTIC COUPLING; DUAL CATALYSIS; ENANTIOSELECTIVE; MICHAEL ACCEPTORS; ORGANOMETALLIC INTERMEDIATES; REACTION MIXTURE; UNSATURATED KETONES;

ALLYLATION; COPPER; KETONES; ORGANOMETALLICS; PALLADIUM;

CATALYSIS;

EID: 84874832510     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201208612     Document Type: Article

References (83)

1. For a review on cooperative multicatalyst systems for one-pot organic transformations, see:, J. M. Lee, Y. Na, H. Han, S. Chang, Chem. Soc. Rev. 2004, 33, 302-312
2. for a review on current tandem catalysis, see:, J.-C. Wasilke, S. J. Obrey, R. T. Baker, G. C. Bazan, Chem. Rev. 2005, 105, 1001-1020.
3. A. Bruggink, R. Schoevaart, T. Kieboom, Org. Process Res. Dev. 2003, 7, 622-640
4. L. M. Ambrosini, T. H. Lambert, ChemCatChem 2010, 2, 1373-1380
5. D. B. Ramachary, S. Jain, Org. Biomol. Chem. 2011, 9, 1277-1300.
6. S. Kamijo, Y. Yamamoto, in Multimetallic Catalysis in Organic Synthesis (Eds.:, M. Shibasaki, Y. Yamamoto,), Wiley-VCH, Weinheim, 2004, pp. 1-52
7. M. H. Pérez-Temprano, J. Casares, P. Espinet, Chem. Eur. J. 2012, 18, 1864-1884
8. J. J. Hirner, Y. Shi, S. A. Blum, Acc. Chem. Res. 2011, 44, 603-613.
9. Y. J. Park, J.-W. Park, C.-H. Jun, Acc. Chem. Res. 2008, 41, 222-234
10. Z. Shao, H. Zhang, Chem. Soc. Rev. 2009, 38, 2745-2755
11. M. Rueping, R. M. Koenigs, I. Atodiresei, Chem. Eur. J. 2010, 16, 9350-9365
12. D. DiRocco, T. Rovis, J. Am. Chem. Soc. 2012, 134, 8094-8097
13. Z. Chai, T. Rainey, J. Am. Chem. Soc. 2012, 134, 3615-3618
14. Y. Ye, M. Sanford, J. Am. Chem. Soc. 2012, 134, 9034-9037.
15. O. Pàmies, J.-E. Baeckvall, Chem. Rev. 2003, 103, 3247-3261
16. C. Zhong, X. Shi, Eur. J. Org. Chem. 2010, 2999-3025
17. J. H. Lee, K. Han, M.-J. Kim, J. Park, Eur. J. Org. Chem. 2010, 999-1015
18. B. L. Conley, M. K. Pennington-Boggio, E. Boz, T. J. Williams, Chem. Rev. 2010, 110, 2294-2312
19. A. C. Marr, S. Liu, Trends Biotechnol. 2011, 29, 199-204.
20. J. Cossy, F. Bargiggia, S. BouzBouz, Org. Lett. 2003, 5, 459-462
21. Y. Nishibayashi, M. Yoshikawa, Y. Inada, M. Hidai, S. Uemura, J. Am. Chem. Soc. 2004, 126, 16066-16072
22. A. S. Goldman, A. H. Roy, Z. Huang, R. Ahuja, W. Schinski, M. Brookhart, Science 2006, 312, 257-261
23. T. A. Cernak, T. H. Lambert, J. Am. Chem. Soc. 2009, 131, 3124-3125
24. K. Takahashi, M. Yamashita, T. Ichihara, K. Nakano, K. Nozaki, Angew. Chem. 2010, 122, 4590-4592
25. Angew. Chem. Int. Ed. 2010, 49, 4488-4490
26. M. Kuriyama, T. Takeichi, M. Ito, N. Yamasaki, R. Yamamura, Y. Demizu, O. Onomura, Chem. Eur. J. 2012, 18, 2477-2480
27. K. Motoyama, M. Ikeda, Y. Miyake, Y. Nishibayashi, Organometallics 2012, 31, 3426-3430
28. E. Skucas, D. Macmillan, J. Am. Chem. Soc. 2012, 134, 9090-9093
29. J. Park, S. Hong, Chem. Soc. Rev. 2012, 41, 6931-6943.
30. M. Sawamura, M. Sudoh, Y. Ito, J. Am. Chem. Soc. 1996, 118, 3309-3310
31. B. Trost, X. Luan, J. Am. Chem. Soc. 2011, 133, 1706-1709
32. B. Trost, X. Luan, Y. Miller, J. Am. Chem. Soc. 2011, 133, 12824-12833
33. J. Panteleev, L. Zhang, M. Lautens, Angew. Chem. 2011, 123, 9255-9258
34. Angew. Chem. Int. Ed. 2011, 50, 9089-9092
35. E. Shirakawa, D. Ikeda, S. Masui, M. Yoshida, T. Hayashi, J. Am. Chem. Soc. 2012, 134, 272-279
36. Z. Gu, A. T. Herrmann, A. Zakarian, Angew. Chem. 2011, 123, 7274-7277
37. Angew. Chem. Int. Ed. 2011, 50, 7136-7139.
38. J. Keith, P. Henry, Angew. Chem. 2009, 121, 9200-9212
39. Angew. Chem. Int. Ed. 2009, 48, 9038-9049, and references there.
40. K. Sonogashira, in Metal-Catalyzed Reactions (Eds.:, F. Diederich, P. J. Stang,), Wiley-VCH, New York, 1998, pp. 203-229
41. K. C. Nicolaou, P. G. Bulger, D. Sarlah, Angew. Chem. 2005, 117, 4516-4563
42. Angew. Chem. Int. Ed. 2005, 44, 4442-4489
43. R. Chinchilla, C. Nájera, Chem. Rev. 2007, 107, 874-922
44. H. Doucet, J.-C. Hierso, Angew. Chem. 2007, 119, 850-888
45. Angew. Chem. Int. Ed. 2007, 46, 834-871.
46. J. Deschamp, T. Hermant, O. Riant, Tetrahedron 2012, 68, 3457-3467
47. A. Welle, V. Cirriez, O. Riant, Tetrahedron 2012, 68, 3435-3443
48. A. Welle, J. Petrignet, B. Tinant, J. Wouters, O. Riant, Chem. Eur. J. 2010, 16, 10980-10983
49. J. Deschamp, O. Riant, Org. Lett. 2009, 11, 1217-1220
50. J. Deschamp, O. Chuzel, J. Hannedouche, O. Riant, Angew. Chem. 2006, 118, 1314-1319
51. Angew. Chem. Int. Ed. 2006, 45, 1292-1297
52. O. Chuzel, J. Deschamp, C. Chausteur, O. Riant, Org. Lett. 2006, 8, 5943-5946
53. A. Welle, S. Diez-Gonzalez, B. Tinant, S. P. Nolan, O. Riant, Org. Lett. 2006, 8, 6059-6062.
54. B. Trost, G. Schroeder, Chem. Eur. J. 2005, 11, 174-184
55. B. M. Trost, Chem. Pharm. Bull. 2002, 50, 1-14
56. B. M. Trost, D. L. Van Vranken, Chem. Rev. 1996, 96, 395-422
57. B. M. Trost, Acc. Chem. Res. 1996, 29, 355-364
58. D. C. Behenna, Y. Liu, T. Yurino, J. Kim, D. E. White, S. C. Virgil, B. M. Stoltz, Nat. Chem. 2012, 4, 130-133.
59. X. Zhao, D. Liu, H. Guo, Y. Liu, W. Zhang, J. Am. Chem. Soc. 2011, 133, 19354-19357
60. J. Weaver, A. Recio, A. Grenning, J. Tunge, Chem. Rev. 2011, 111, 1846-1913
61. B. Trost, J. Xu, T. Schmidt, J. Am. Chem. Soc. 2009, 131, 18343-18357
62. B. Trost, B. Schäffner, M. Osipov, D. A. Wilton, Angew. Chem. 2011, 123, 3610-3613
63. Angew. Chem. Int. Ed. 2011, 50, 3548-3551
64. A. Doyle, E. Jacobsen, J. Am. Chem. Soc. 2005, 127, 62-63
65. E. Bélanger, K. Cantin, O. Messe, M. Tremblay, J.-F. Paquin, J. Am. Chem. Soc. 2007, 129, 1034-1035
66. D. C. Behenna, B. M. Stoltz, J. Am. Chem. Soc. 2004, 126, 15044-15045
67. D. C. Behenna, B. M. Stoltz, J. T. Mohr, A. M. Harned, US Patent, 0,084,820, 2006
68. A. Y. Hong, M. R. Krout, T. Jensen, N. B. Bennett, A. M. Harned, B. M. Stoltz, Angew. Chem. 2011, 123, 2808-2812
69. Angew. Chem. Int. Ed. 2011, 50, 2756-2760
70. H. Mukherjee, N. T. McDougal, S. C. Virgil, B. M. Stoltz, Org. Lett. 2011, 13, 825-827
71. N. B. Bennett, A. Y. Hong, A. M. Harned, B. M. Stoltz, Org. Biomol. Chem. 2012, 10, 56-59
72. B. Stoltz, et al., Chem. Eur. J. 2011, 17, 14199-14223
73. J. Tsuji, I. Minami, I. Shimizu, Chem. Lett. 1983, 1325-1326
74. J. Tsuji, I. Minami, I. Shimizu, H. Kataoka, Chem. Lett. 1984, 1133-1136.
75. M. Shimizu, Angew. Chem. 2011, 123, 6122-6124
76. Angew. Chem. Int. Ed. 2011, 50, 5998-6000
77. B. M. Wang, Y. Q. Tu, Acc. Chem. Res. 2011, 44, 1207-1222
78. J. Christoffers, A. Baro, Quaternary Stereocenters-Challenges and Solutions for Organic Synthesis, Wiley-VCH, Weinheim, 2005.
79. N. P. Mankad, D. S. Laitar, J. P. Sadighi, Organometallics 2004, 23, 3369-3371.
80. J. L. van der Baan, F. Bieckehaupt, Tetrahedron 1986, 27, 6267-6270
81. P. von Matt, A. Pfaltz, Angew. Chem. 1993, 105, 614-615
82. Angew. Chem. Int. Ed. Engl. 1993, 32, 566-568
83. K. Tani, D. C. Behenna, R. M. McFadden, B. M. Stoltz, Org. Lett. 2007, 9, 2529-2531.