Chiral counteranion strategy for asymmetric oxidative C(sp3)-H/C(sp3)-H coupling: Enantioselective α-allylation of aldehydes with terminal alkenes

Angewandte Chemie - International Edition

Volumn 53, Issue 45, 2014, Pages 12218-12221

  Wang, Pu Sheng ^a   Lin, Hua Chen ^a   Zhai, Yu Jia ^a   Han, Zhi Yong ^a   Gong, Liu Zhu ^a,b  

^a UNIVERSITY OF SCIENCE AND TECHNOLOGY OF CHINA   (China)

^b SynBio Research Platform   (China)

Author keywords

allylic compounds; C H activation; cross coupling; enantioselectivity; palladium

Indexed keywords

ACTIVATION ANALYSIS; ALDEHYDES; ALLYLATION; AROMATIC COMPOUNDS; CATALYSIS; CHEMICAL ACTIVATION; CHEMICAL REACTIONS; HYDROCARBONS; PALLADIUM;

ALLYLATION PRODUCTS; ALLYLIC COMPOUNDS; AROMATIC ALDEHYDE; C-H ACTIVATION; COUPLING REACTION; CROSS-COUPLINGS; ENANTIOSELECTIVE; PALLADIUM-CATALYZED;

ENANTIOSELECTIVITY;

EID: 84941116716     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201408199     Document Type: Article

References (93)

1. E. J. Corey, X. M. Cheng, The Logic of Chemical Synthesis, Wiley, New York 1989;
2. C.-J. Li, Chem. Rev. 2005, 105, 3095;
3. R. A. Sheldon, I. W. C. E. Arends, U. Hanefeld, Green Chemistry and Catalysis, Wiley-VCH, Weinheim, 2007, p. 223.
4. G. A. Molander, C. R. Harris, Chem. Rev. 1996, 96, 307;
5. J. Hassan, M. Sévignon, C. Gozzi, E. Schulz, M. Lemaire, Chem. Rev. 2002, 102, 1359;
6. K. C. Nicolaou, S. A. Snyder, T. Montagnon, G. Vassilikogiannakis, Angew. Chem. Int. Ed. 2002, 41, 1668;
7. Angew. Chem. 2002, 114, 1742;
8. V. Ritleng, C. Sirlin, M. Pfeffer, Chem. Rev. 2002, 102, 1731;
9. F. Kakiuchi, N. Chatani, Adv. Synth. Catal. 2003, 345, 1077;
10. M. Bandini, A. Melloni, A. Umani-Ronchi, Angew. Chem. Int. Ed. 2004, 43, 550;
11. Angew. Chem. 2004, 116, 560;
12. W. Notz, F. Tanaka, C. F. Barbas III, Acc. Chem. Res. 2004, 37, 580;
13. B. M. Trost, J. Org. Chem. 2004, 69, 5813;
14. X. Chen, K. M. Engle, D.-H. Wang, J.-Q. Yu, Angew. Chem. Int. Ed. 2009, 48, 5094;
15. Angew. Chem. 2009, 121, 5196;
16. R. Giri, B.-F. Shi, K. M. Engle, N. Maugel, J.-Q. Yu, Chem. Soc. Rev. 2009, 38, 3242.
17. C.-J. Li, Acc. Chem. Res. 2009, 42, 335;
18. C. J. Scheuermann, Chem. Asian J. 2010, 5, 436;
19. C. Liu, H. Zhang, W. Shi, A. Lei, Chem. Rev. 2011, 111, 1780;
20. C. S. Yeung, V. M. Dong, Chem. Rev. 2011, 111, 1215;
21. B.-J. Li, Z.-J. Shi, Chem. Soc. Rev. 2012, 41, 5588;
22. S. A. Girard, T. Knauber, C.-J. Li, Angew. Chem. Int. Ed. 2014, 53, 74;
23. Angew. Chem. 2014, 126, 76.
24. Z. Li, C.-J. Li, Org. Lett. 2004, 6, 4997;
25. C. Guo, J. Song, L.-Z. Gong, Angew. Chem. Int. Ed. 2010, 49, 5558;
26. Angew. Chem. 2010, 122, 5690;
27. G. Zhang, Y. Zhang, R. Wang, Angew. Chem. Int. Ed. 2011, 50, 10429;
28. Angew. Chem. 2011, 123, 10613;
29. J. Zhang, B. Tiwari, C. Xing, X. Chen, Y. Chi, Angew. Chem. Int. Ed. 2012, 51, 3649;
30. Angew. Chem. 2012, 124, 3709;
31. G. Zhang, Y. Ma, S. Wang, Y. Zhang, R. Wang, J. Am. Chem. Soc. 2012, 134, 12334;
32. G. Zhang, Y. Ma, S. Wang, W. Kong, R. Wang, Chem. Sci. 2013, 4, 2645;
33. Y. Cui, L. Villafane, D. Clausen, P. Floreancig, Tetrahedron 2013, 69, 7618;
34. B. M. Trost, D. A. Thaisrivongs, E. J. Donckele, Angew. Chem. Int. Ed. 2013, 52, 1523;
35. Angew. Chem. 2013, 125, 1563;
36. A. J. Neel, J. P. Hehn, P. F. Tripet, F. D. Toste, J. Am. Chem. Soc. 2013, 135, 14044.
37. R. J. Phipps, G. L. Hamilton, F. D. Toste, Nat. Chem. 2012, 4, 603;
38. M. Mahlau, B. List, Angew. Chem. Int. Ed. 2013, 52, 518;
39. Angew. Chem. 2013, 125, 540;
40. K. Brak, E. N. Jacobsen, Angew. Chem. Int. Ed. 2013, 52, 534;
41. Angew. Chem. 2013, 125, 558.
42. P.-S. Wang, X.-L. Zhou, L.-Z. Gong, Org. Lett. 2014, 16, 976;
43. Z.-L. Tao, W.-Q. Zhang, D.-F. Chen, A. Adele, L.-Z. Gong, J. Am. Chem. Soc. 2013, 135, 9255.
44. P.-S. Wang, H.-C. Lin, X. L. Zhou, L.-Z. Gong, Org. Lett. 2014, 16, 3332.
45. Z. Li, C.-J. Li, J. Am. Chem. Soc. 2005, 127, 6968;
46. S. Lin, C.-X. Song, G.-X. Cai, W.-H. Wang, Z.-J. Shi, J. Am. Chem. Soc. 2008, 130, 12901;
47. A. J. Young, M. C. White, J. Am. Chem. Soc. 2008, 130, 14090;
48. A. J. Young, M. C. White, Angew. Chem. Int. Ed. 2011, 50, 6824;
49. Angew. Chem. 2011, 123, 6956;
50. B. M. Trost, M. M. Hansmann, D. A. Thaisrivongs, Angew. Chem. Int. Ed. 2012, 51, 4950;
51. Angew. Chem. 2012, 124, 5034;
52. L. Li, Q.-Y. Chen, Y. Guo, Chem. Commun. 2013, 49, 8764;
53. J. M. Howell, W. Liu, A. J. Young, M. C. White, J. Am. Chem. Soc. 2014, 136, 5750;
54. during preparation of the manuscript, Luo, Lei and co-workers reported a nonselective allylation reaction of ketones using Pd/amine cooperative catalysis:, S. Tang, X. Wu, W. Liao, K. Liu, C. Liu, S. Luo, A. Lei, Org. Lett. 2014, 16, 3584.
55. D. J. Covell, M. C. White, Angew. Chem. Int. Ed. 2008, 47, 6448;
56. Angew. Chem. 2008, 120, 6548;
57. H. Du, B. Zhao, Y. Shi, J. Am. Chem. Soc. 2008, 130, 8590;
58. B. Zhao, H. Du, R. Fu, Y. Shi, Org. Synth. 2010, 87, 263;
59. A. Sharma, J. F. Hartwig, J. Am. Chem. Soc. 2013, 135, 17983; for a review, see:
60. T. A. Ramirez, B. G. Zhao, Y. Shi, Chem. Soc. Rev. 2012, 41, 931.
61. S. Mukherjee, B. List, J. Am. Chem. Soc. 2007, 129, 11336;
62. G. Jiang, B. List, Angew. Chem. Int. Ed. 2011, 50, 9471;
63. II/chiral phosphoric acid cooperative catalysis, see:
64. H. Alper, N. Hamel, J. Am. Chem. Soc. 1990, 112, 2803;
65. Z. Chai, T.-J. Rainey, J. Am. Chem. Soc. 2012, 134, 3615;
66. S.-Y. Yu, H. Zhang, Y. Gao, L. Mo, S. Wang, Z.-J. Yao, J. Am. Chem. Soc. 2013, 135, 11402.
67. G. Chen, Y. Deng, L. Gong, A. Mi, X. Cui, Y. Jiang, M. C. K. Choi, A. S. C. Chan, Tetrahedron: Asymmetry 2001, 12, 1567;
68. M. Nakoji, T. Kanayama, T. Okino, Y. Takemoto, Org. Lett. 2001, 3, 3329;
69. M. Nakoji, T. Kanayama, T. Okino, Y. Takemoto, J. Org. Chem. 2002, 67, 7418;
70. B. G. Jellerichs, J.-R. Kong, M. J. Krische, J. Am. Chem. Soc. 2003, 125, 7758; for reviews, see:
71. Z.-H. Shao, H.-B. Zhang, Chem. Soc. Rev. 2009, 38, 2745;
72. Z. T. Du, Z.-H. Shao, Chem. Soc. Rev. 2013, 42, 1337;
73. A. E. Allen, D. W. C. MacMillan, Chem. Sci. 2012, 3, 633;
74. Z.-Y. Han, C. Wang, L.-Z. Gong, in Science of Synthesis: Asymmetric Organocatalysis, Vol. 2 (Ed.:, K. Maruoka,), Georg Thieme, Stuttgart, 2012, p. 697;
75. D.-F. Chen, Z.-Y. Han, X.-L. Zhou, L.-Z. Gong, Acc. Chem. Res. 2014, 47, 2365.
76. N. T. Patil, H. Wu, I. Kadota, Y. Yamamoto, J. Org. Chem. 2004, 69, 8745;
77. M. Yoshida, T. Terumine, E. Masaki, S. Hara, J. Org. Chem. 2013, 78, 10853;
78. S. Krautwald, D. Sarlah, M. A. Schafroth, E. M. Carreira, Science 2013, 340, 1065;
79. M. Yoshida, E. Masaki, T. Terumine, S. Hara, Synthesis 2014, 1367;
80. S. Krautwald, M. A. Schafroth, D. Sarlah, E. M. Carreira, J. Am. Chem. Soc. 2014, 136, 3020.
81. J. Muzart, Eur. J. Org. Chem. 2010, 3779.
82. B. Tiwari, J. Zhang, Y. R. Chi, Angew. Chem. Int. Ed. 2012, 51, 1911;
83. Angew. Chem. 2012, 124, 1947.
84. T. Akiyama, Chem. Rev. 2007, 107, 5744;
85. D. Kampen, C. M. Reisinger, B. List, Top. Curr. Chem. 2009, 291, 395;
86. M. Terada, Synthesis 2010, 1929;
87. M. Terada, Curr. Org. Chem. 2011, 15, 2227;
88. J. Yu, F. Shi, L.-Z. Gong, Acc. Chem. Res. 2011, 44, 1156; for a review on the application of TRIP in asymmetric organocatalysis, see:
89. G. Adair, S. Mukherjee, B. List, Aldrichimica Acta 2008, 41, 31.
90. M. Higuchi, I. Ikeda, T. Hirao, J. Org. Chem. 1997, 62, 1072;
91. H. Hamamoto, Y. Suzuki, H. Takahashi, S. Ikegami, Tetrahedron Lett. 2007, 48, 4239;
92. M. O. Ratnikov, L. E. Farkas, E. C. McLaughlin, G. Chiou, H. Choi, S. H. El-Khalafy, M. P. Doyle, J. Org. Chem. 2011, 76, 2585;
93. D.-S. Kim, J.-W. Park, C.-H. Jun, Adv. Synth. Catal. 2013, 355, 2667.