Chiral primary amine/palladium dual catalysis for asymmetric allylic alkylation of β-ketocarbonyl compounds with allylic alcohols

Angewandte Chemie - International Edition

Volumn 54, Issue 43, 2015, Pages 12645-12648

  Zhou, Han ^a   Zhang, Long ^a   Xu, Changming ^a   Luo, Sanzhong ^a  

^a INSTITUTE OF CHEMISTRY   (China)

Author keywords

allylic alcohols; asymmetric allylic alkylation; chiral primary amines; palladium; ketocarbonyl compounds

Indexed keywords

ALLYLATION; AMINES; CATALYSTS; KETONES; PALLADIUM; PALLADIUM COMPOUNDS;

ALIPHATIC KETONES; ALLYLIC ALCOHOL; ASYMMETRIC ALLYLIC ALKYLATIONS; CATALYTIC SYSTEM; HIGH ENANTIOSELECTIVITY; PALLADIUM COMPLEXES; PRIMARY AMINES; QUATERNARY STEREOCENTERS;

ALKYLATION;

EID: 84944249956     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201505946     Document Type: Article

References (68)

1. B. M. Trost, D. L. van Vranken, Chem. Rev. 1996, 96, 395;
2. B. M. Trost, Acc. Chem. Res. 1996, 29, 355;
3. B. M. Trost, M. L. Crawley, Chem. Rev. 2003, 103, 2921;
4. B. M. Trost, M. R. Machacek, A. Aponick, Acc. Chem. Res. 2006, 39, 747;
5. Z. Lu, S. Ma, Angew. Chem. Int. Ed. 2008, 47, 258;
6. Angew. Chem. 2008, 120, 264.
7. J. Tsuji, H. Takahashi, M. Morikawa, Tetrahedron Lett. 1965, 6, 4387;
8. K. Hiroi, J. Abe, K. Suya, S. Sato, T. Koyama, J. Org. Chem. 1994, 59, 203;
9. D. J. Weix, J. F. Hartwig, J. Am. Chem. Soc. 2007, 129, 7720;
10. S. Mukherjee, B. List, J. Am. Chem. Soc. 2007, 129, 11336;
11. X. Zhao, D. Liu, H. Guo, Y. Liu, W. Zhang, J. Am. Chem. Soc. 2011, 133, 19354;
12. M. Chiarucci, M. di Lillo, A. Romaniello, P. G. Cozzi, G. Cera, M. Bandini, Chem. Sci. 2012, 3, 2859.
13. Z. H. Shao, H.-B. Zhang, Chem. Soc. Rev. 2009, 38, 2745;
14. C. Zhong, X.-D. Shi, Eur. J. Org. Chem. 2010, 2999;
15. A. E. Allen, D. W. C. MacMillan, Chem. Sci. 2012, 3, 633;
16. Z.-T. Du, Z.-H. Shao, Chem. Soc. Rev. 2013, 42, 1337;
17. Y. Deng, S. Kumar, H. Wang, Chem. Commun. 2014, 50, 4272.
18. G. X. Jiang, B. List, Angew. Chem. Int. Ed. 2011, 50, 9471;
19. Angew. Chem. 2011, 123, 9643;
20. S. Afewerki, I. Ibrahem, J. Rydfjord, P. Breistein, A. Cõrdova, Chem. Eur. J. 2012, 18, 2972;
21. S. Krautwald, D. Sarlah, M. A. Schafroth, E. M. Carreira, Science 2013, 340, 1065;
22. S. Krautwald, M. S. Schafroth, D. Sarlah, E. M. Carreira, J. Am. Chem. Soc. 2014, 136, 3020; for examples with cyclic ketones, see:
23. I. Ibrahem, A. Cõrdova, Angew. Chem. Int. Ed. 2006, 45, 1952;
24. Angew. Chem. 2006, 118, 1986 (see the Supporting Information: up to 20-% yield and 88-% ee);
25. M. Shibasaki, N. Kumagai, S. Yasuda, Heterocycles 2012, 86, 745 (up to 66-% yield and 60-% ee).
26. R. Kuwano, Y. Ito, J. Am. Chem. Soc. 1999, 121, 3236;
27. B. M. Trost, G. M. Schroeder, J. Am. Chem. Soc. 1999, 121, 6759;
28. B. M. Trost, G. M. Schroeder, J. Kristensen, Angew. Chem. Int. Ed. 2002, 41, 3492;
29. Angew. Chem. 2002, 114, 3642;
30. X.-X. Yan, C.-G. Liang, Y. Zhang, W. Hong, B.-X. Cao, L.-X. Dai, X.-L. Hou, Angew. Chem. Int. Ed. 2005, 44, 6544;
31. Angew. Chem. 2005, 117, 6702;
32. T. Nemoto, T. Matsumoto, T. Masuda, T. Hitomi, K. Hatano, Y. Hamada, J. Am. Chem. Soc. 2004, 126, 3690;
33. W.-H. Zheng, B.-H. Zheng, Y. Zhang, X.-L. Hou, J. Am. Chem. Soc. 2007, 129, 7718;
34. B.-L. Lei, C.-H. Ding, X.-F. Yang, X.-L. Wan, X.-L. Hou, J. Am. Chem. Soc. 2009, 131, 18250;
35. J.-P. Chen, C.-H. Ding, W. Liu, X.-H. Hou, L.-X. Dai, J. Am. Chem. Soc. 2010, 132, 15493;
36. W. Chen, M. Chen, J. F. Hartwig, J. Am. Chem. Soc. 2014, 136, 15825.
37. Y. Tamaru, Eur. J. Org. Chem. 2005, 2647;
38. J. Muzart, Tetrahedron 2005, 61, 4179;
39. M. Bandini, Angew. Chem. Int. Ed. 2011, 50, 994;
40. Angew. Chem. 2011, 123, 1026;
41. B. Sundararaju, M. Achard, C. Bruneau, Chem. Soc. Rev. 2012, 41, 4467;
42. M. Bandini, G. Cera, M. Chiarucci, Synthesis 2012, 504; for selected examples, see:
43. I. Usui, S. Schmidt, B. Breit, Org. Lett. 2009, 11, 1453;
44. X. Huo, M. Quan, G. Yang, X. Zhao, D. Liu, Y. Liu, W. Zhang, Org. Lett. 2014, 16, 1570;
45. R. Shibuya, L. Lin, Y. Nakahara, K. Mashima, T. Ohshima, Angew. Chem. Int. Ed. 2014, 53, 4377;
46. Angew. Chem. 2014, 126, 4466;
47. X. Huo, G. Yang, D. Liu, Y, Liu, I. D. Gridnev, W, Zhang, Angew. Chem. Int. Ed. 2014, 53, 6776;
48. Angew. Chem. 2014, 126, 6894.
49. Z.-L. Tao, W.-Q. Zhang, D.-F. Chen, A. Adele, L.-Z. Gong, J. Am. Chem. Soc. 2013, 135, 9255;
50. D. Banerjee, K. Junge, M. Beller, Angew. Chem. Int. Ed. 2014, 53, 13049;
51. Angew. Chem. 2014, 126, 13265.
52. M. Sawamura, H. Nagata, H. Sakamoto, Y. Ito, J. Am. Chem. Soc. 1992, 114, 2586;
53. B. M. Trost, R. Radinov, E. M. Grenzer, J. Am. Chem. Soc. 1997, 119, 7870;
54. R. Kuwano, K. Uchida, Y. Ito, Org. Lett. 2003, 5, 2177;
55. B. M. Trost, D. A. Thaisrivongs, E. J. Donckele, Angew. Chem. Int. Ed. 2013, 52, 1523;
56. Angew. Chem. 2013, 125, 1563;
57. B. M. Trost, E. J. Donckele, D. A. Thaisrivongs, M. Osipov, J. T. Masters, J. Am. Chem. Soc. 2015, 137, 2776; for an example of an iridium-catalyzed AAA reaction with cyclic β-ketoesters, see:
58. W.-B. Liu, C. M. Reeves, S. C. Virgil, B. M. Stoltz, J. Am. Chem. Soc. 2013, 135, 10626.
59. R. Kuwano, R. Nishio, Y. Ito, Org. Lett. 1999, 1, 837; for an example of an iridium-catalyzed AAA reaction with acyclic β-ketoesters, see:
60. B. M. Stoltz, W.-B. Liu, C. M. Reeves, J. Am. Chem. Soc. 2013, 135, 17298.
61. C. Xu, L. Zhang, S. Luo, Angew. Chem. Int. Ed. 2014, 53, 4149;
62. Angew. Chem. 2014, 126, 4233;
63. Y. Zhu, L. Zhang, S. Luo, J. Am. Chem. Soc. 2014, 136, 14642.
64. P. Trillo, A. Baeza, C. Nájera, Eur. J. Org. Chem. 2012, 2929;
65. R. Sanz, A. Martínez, D. Miguel, J. M. Álvarez-Gutiérrez, F. Rodríguez, Adv. Synth. Catal. 2006, 348, 1841.
66. D. Wang, C. Xu, L. Zhang, S. Luo, Org. Lett. 2015, 17, 576.
67. L. Zhang, N. Fu, S. Luo, Acc. Chem. Res. 2015, 48, 986;
68. C. Xu, L. Zhang, S. Luo, J. Org. Chem. 2014, 79, 11517.