Design of a combinational magnesium catalyst for the stereocontrolled cross reaction of enones

Chemistry - A European Journal

Volumn 20, Issue 28, 2014, Pages 8584-8588

  Yang, Dongxu ^a   Wang, Linqing ^a   Han, Fengxia ^a   Zhao, Depeng ^a   Wang, Rui ^a,b  

^a LANZHOU UNIVERSITY   (China)

^b LANZHOU INSTITUTE OF CHEMICAL PHYSICS   (China)

Author keywords

cyclization; enantioselectivity; intermolecular symmetric structure; magnesium catalysts; site specific selectivity

Indexed keywords

CATALYST SELECTIVITY; CYCLIZATION; FUNCTIONAL GROUPS; MAGNESIUM;

CROSS REACTION; MAGNESIUM CATALYSTS; REACTION PARTNERS; SITE-SPECIFIC; SYMMETRIC STRUCTURES;

ENANTIOSELECTIVITY;

EID: 84903688811     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201403183     Document Type: Article

References (108)

1. G. Casiraghi, L. Battistini, C. Curti, G. Rassu, F. Zanardi, Chem. Rev. 2011, 111, 3076
2. J. Clayden, Chem. Soc. Rev. 2009, 38, 817
3. S. F. Martin, Acc. Chem. Res. 2002, 35, 895
4. S. E. Denmark, J. R. Heemstra, Jr., G. L. Beutner, Angew. Chem. 2005, 117, 4760
5. Angew. Chem. Int. Ed. 2005, 44, 4682.
6. K. L. Jensen, G. Dickmeiss, H. Jiang, Ł. Albrecht, K. A. Jørgensen, Acc. Chem. Res. 2012, 45, 248
7. J.-L. Li, T.-Y. Liu, Y.-C. Chen, Acc. Chem. Res. 2012, 45, 1491
8. H. Jiang, Ł. Albrecht, K. A. Jørgensen, Chem. Sci. 2013, 4, 2287
9. I. Jurberg, I. Chatterjee, R. Tannert, P. Melchiorre, Chem. Commun. 2013, 49, 4869; for selected recent representative examples
10. H. Jiang, D. C. Cruz, Y. Li, V. H. Lauridsen, K. A. Jørgensen, J. Am. Chem. Soc. 2013, 135, 5200
11. X. Feng, Z. Zhou, C. Ma, X. Yin, R. Li, L. Dong, Y.-C. Chen, Angew. Chem. 2013, 125, 14423
12. Angew. Chem. Int. Ed. 2013, 52, 14173
13. D. Bastida, Y. Liu, X. Tian, E. Escudero-Adán, P. Melchiorre, Org. Lett. 2013, 15, 220
14. Ł. Albrecht, G. Dickmeiss, F. C. Acosta, C. Rodrìguez- Escrich, R. L. Davis, K. A. Jørgensen, J. Am. Chem. Soc. 2012, 134, 2543
15. G. Talavera, E. Reyes, J. L. Vicario, L. Carrillo, Angew. Chem. 2012, 124, 4180
16. Angew. Chem. Int. Ed. 2012, 51, 4104
17. J.-L. Li, S.-L. Zhou, P.-Q. Chen, L. Dong, T.-Y. Liu, Y.-C. Chen, Chem. Sci. 2012, 3, 1879
18. C. Cassani, P. Melchiorre, Org. Lett. 2012, 14, 5590
19. G. Bencivennia, P. Galzeranoa, A. Mazzantia, G. Bartolia, P. Melchiorre, Proc. Natl. Acad. Sci. USA 2010, 107, 20642
20. G. Bergonzini, S. Vera, P. Melchiorre, Angew. Chem. 2010, 122, 9879
21. Angew. Chem. Int. Ed. 2010, 49, 9685
22. J.-L. Li, T.-R. Kang, S.-L. Zhou, R. Li, L. Wu, Y.-C. Chen, Angew. Chem. 2010, 122, 6562
23. Angew. Chem. Int. Ed. 2010, 49, 6418
24. R. M. de Figueiredo, R. Fröhlich, M. Christmann, Angew. Chem. 2008, 120, 1472
25. Angew. Chem. Int. Ed. 2008, 47, 1450
26. S. Bertelsen, M. Marigo, S. Brandes, P. Dinér, K. A. Jørgensen, J. Am. Chem. Soc. 2006, 128, 12973.
27. J. Xu, Z. Jin, Y. R. Chi, Org. Lett. 2013, 15, 5028
28. J. Mo, X. Chen, Y. R. Chi, J. Am. Chem. Soc. 2012, 134, 8810
29. H. Ube, N. Shimada, M. Terada, Angew. Chem. 2010, 122, 1902
30. Angew. Chem. Int. Ed. 2010, 49, 1858
31. J. Luo, H. Wang, X. Han, L.-W. Xu, J. Kwiatkowski, K.-W. Huang, Y. Lu, Angew. Chem. 2011, 123, 1901
32. Angew. Chem. Int. Ed. 2011, 50, 1861
33. H. Huang, Z. Jin, K. Zhu, X. Liang, J. Ye, Angew. Chem. 2011, 123, 3290
34. Angew. Chem. Int. Ed. 2011, 50, 3232
35. C. Curti, G. Rassu, V. Zambrano, L. Pinna, G. Pelosi, A. Sartori, L. Battistini, F. Zanardi, G. Casiraghi, Angew. Chem. 2012, 124, 6304
36. Angew. Chem. Int. Ed. 2012, 51, 6200
37. X. Jiang, L. Liu, P. Zhang, Y. Zhong, R. Wang, Angew. Chem. 2013, 125, 11539
38. Angew. Chem. Int. Ed. 2013, 52, 11329
39. J. Zhang, X. Liu, X. Ma, R. Wang, Chem. Commun. 2013, 49, 9329
40. P. S. Tiseni, R. Peters, Angew. Chem. 2007, 119, 5419
41. Angew. Chem. Int. Ed. 2007, 46, 5325
42. L. Shen, L. Sun, S. Ye, J. Am. Chem. Soc. 2011, 133, 15894
43. L. Shen, W.-Q. Jia, S. Ye, Angew. Chem. 2013, 125, 613
44. Angew. Chem. Int. Ed. 2013, 52, 585.
45. B. M. Trost, J. Hitce, J. Am. Chem. Soc. 2009, 131, 4572
46. A. Yamaguchi, S. Matsunaga, M. Shibasaki, Org. Lett. 2008, 10, 2319
47. N. E. Shepherd, H. Tanabe, Y. Xu, S. Matsunaga, M. Shibasaki, J. Am. Chem. Soc. 2010, 132, 3666
48. L. Yin, H. Takada, N. Kumagai, M. Shibasaki, Angew. Chem. 2013, 125, 7451
49. Angew. Chem. Int. Ed. 2013, 52, 7310
50. L. Lin, J. Zhang, X. Ma, X. Fu, R. Wang, Org. Lett. 2011, 13, 6410.
51. D. Yang, L. Wang, F. Han, D. Zhao, B. Zhang, R. Wang, Angew. Chem. 2013, 125, 6871
52. Angew. Chem. Int. Ed. 2013, 52, 6739.
53. L. Dell Amico, Ł. Albrecht, T. Naicker, P. H. Poulsen, K. A. Jørgensen, J. Am. Chem. Soc. 2013, 135, 8063.
54. M. Terada, F. Li, Y. Toda, Angew. Chem. 2014, 126, 239
55. Angew. Chem. Int. Ed. 2014, 53, 235
56. K. Saito, Y. Kajiwara, T. Akiyama, Angew. Chem. 2013, 125, 13526
57. Angew. Chem. Int. Ed. 2013, 52, 13284
58. S.-Y. Yu, H. Zhang, Y. Gao, L. Mo, S. Wang, Z.-J. Yao, J. Am. Chem. Soc. 2013, 135, 11402
59. R. J. Phipps, F. D. Toste, J. Am. Chem. Soc. 2013, 135, 1268
60. W. Chen, J. F. Hartwig, J. Am. Chem. Soc. 2013, 135, 2068
61. B. Xu, S.-F. Zhu, Z.-C. Zhang, Z. Yu, Y. Ma, Q.-L. Zhou, Chem. Sci. 2014, 5, 1442
62. G. L. Li, T. Liang, L. Wojtas, J. C. Antilla, Angew. Chem. 2013, 125, 4726
63. Angew. Chem. Int. Ed. 2013, 52, 4628
64. J. Lv, L. Zhang, S. Z. Luo, J.-P. Cheng, Angew. Chem. 2013, 125, 9968
65. Angew. Chem. Int. Ed. 2013, 52, 9786
66. Y.-M. Wang, J. Wu, C. Hoong, V. Rauniyar, F. D. Toste, J. Am. Chem. Soc. 2012, 134, 12928
67. A. Alix, C. Lalli, P. Retailleau, G. Masson, J. Am. Chem. Soc. 2012, 134, 10389
68. E. L. McInturff, E. Yamaguchi, M. J. Krische, J. Am. Chem. Soc. 2012, 134, 20628
69. Z. Chai, T. J. Rainey, J. Am. Chem. Soc. 2012, 134, 3615
70. J. R. Zbieg, E. Yamaguchi, E. L. Mclnturff, M. J. Krische, Science 2012, 336, 324
71. V. Rauniyar, A. D. Lackner, G. L. Hamilton, F. D. Toste, Science 2011, 334, 1681
72. Z. Zhang, W. Zheng, J. C. Antilla, Angew. Chem. 2011, 123, 1167
73. Angew. Chem. Int. Ed. 2011, 50, 1135
74. W. Zheng, Z. Zhang, M. J. Kaplan, J. C. Antilla, J. Am. Chem. Soc. 2011, 133, 3339
75. V. Rauniyar, Z. Wang, H. E. Burks, F. D. Toste, J. Am. Chem. Soc. 2011, 133, 8486
76. G. Jiang, R. Halder, Y. Fang, B. List, Angew. Chem. 2011, 123, 9926
77. Angew. Chem. Int. Ed. 2011, 50, 9752
78. M. Hatano, K. Moriyama, T. Maki, K. Ishihara, Angew. Chem. 2010, 122, 3911
79. Angew. Chem. Int. Ed. 2010, 49, 3823
80. S. Liao, B. List, Angew. Chem. 2010, 122, 638
81. Angew. Chem. Int. Ed. 2010, 49, 628
82. R. L. LaLonde, Z. Wang, M. Mba, A. D. Lackner, F. D. Toste, Angew. Chem. 2010, 122, 608
83. Angew. Chem. Int. Ed. 2010, 49, 598
84. C. Li, C. Wang, B. Villa-Marcos, J. Xiao, J. Am. Chem. Soc. 2008, 130, 14450
85. S. Mukherjee, B. List, J. Am. Chem. Soc. 2007, 129, 11336
86. G. L. Hamilton, E. Kang, M. Mba, F. D. Toste, Science 2007, 317, 496.
87. K. Ohmatsu, M. Ito, T. Kunieda, T. Ooi, J. Am. Chem. Soc. 2013, 135, 590
88. X. Feng, Z. Zhou, R. Zhou, Q.-Q. Zhou, L. Dong, Y.-C. Chen, J. Am. Chem. Soc. 2012, 134, 19942
89. T. Xu, C. Cassani, Y. Liu, Y. Moran, A. Urakawa, P. Galzerano, E. Arceo, P. Melchiorre, J. Am. Chem. Soc. 2011, 133, 17934
90. N. J. A. Martin, B. List, J. Am. Chem. Soc. 2006, 128, 13368
91. S. Mayer, B. List, Angew. Chem. 2006, 118, 4299
92. Angew. Chem. Int. Ed. 2006, 45, 4193.
93. L. Stegbauer, F. Sladojevich, D. J. Dixon, Chem. Sci. 2012, 3, 942; for selected examples
94. S. Kobayashi, Y. Tsuchiya, T. Mukaiyama, Chem. Lett. 1991, 20, 541
95. R. M. Kamble, V. K. Singh, Tetrahedron Lett. 2003, 44, 5347
96. C. Zhu, X. Shen, S. G. Nelson, J. Am. Chem. Soc. 2004, 126, 5352
97. L. Liu, R. Wang, Y.-F. Kang, C. Chen, Z.-Q. Xu, Y.-F. Zhou, M. Ni, H.-Q. Cai, M.-Z. Gong, J. Org. Chem. 2005, 70, 1084
98. S. France, M. H. Shah, A. Weatherwax, H. Wack, J. P. Roth, T. Lectka, J. Am. Chem. Soc. 2005, 127, 1206
99. Z. Liu, A. S. Wasmuth, S. G. Nelson, J. Am. Chem. Soc. 2006, 128, 10352
100. J. Wang, X. Hu, J. Jiang, S. Gou, X. Huang, X. Liu, X. Feng, Angew. Chem. 2007, 119, 8620
101. Angew. Chem. Int. Ed. 2007, 46, 8468
102. F. M. Koch, R. Peters, Angew. Chem. 2007, 119, 2739
103. Angew. Chem. Int. Ed. 2007, 46, 2685
104. F. Yang, D. Zhao, J. Lan, P Xi, L. Yang, S. Xiang, J. You, Angew. Chem. 2008, 120, 5728
105. Angew. Chem. Int. Ed. 2008, 47, 5646
106. S. Cui, S. D. Walker, J. C. S. Woo, C. J. Borths, H. Mukherjee, M. J. Chen, M. M. Faul, J. Am. Chem. Soc. 2010, 132, 436
107. J. Erb, D. H. Paull, T. Dudding, L. Belding, T. Lectka, J. Am. Chem. Soc. 2011, 133, 7536
108. D. Yang, L. Wang, D. Zhao, F. Han, B. Zhang, R. Wang, Chem. Eur. J. 2013, 19, 4691.