Asymmetric dearomatization of β-naphthols through an amination reaction catalyzed by a chiral phosphoric acid

Angewandte Chemie - International Edition

Volumn 54, Issue 2, 2015, Pages 647-650

  Wang, Shou Guo ^a   Yin, Qin ^a   Zhuo, Chun Xiang ^a   You, Shu Li ^a,b  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

^b Tianjin Engineering Center of Micro Nano Biomaterials and Detection Treatment Technology   (China)

Author keywords

Amination reaction; Asymmetric catalysis; Dearomatization; Naphthol; Organocatalysis

Indexed keywords

AMINES; CATALYSIS; NAPHTHOL; PHOSPHORIC ACID; REACTION KINETICS;

AMINATION REACTION; ASYMMETRIC CATALYSIS; DEAROMATIZATION; ELECTROPHILIC AMINATION; FACILE ACCESS; FUNCTIONALIZED; ORGANOCATALYSIS; QUATERNARY CARBON;

AROMATIZATION;

EID: 84922803949     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201409756     Document Type: Article

References (82)

1. a) C.-X. Zhuo, W. Zhang, S.-L. You, Angew. Chem. Int. Ed. 2012, 51, 12662;
2. Angew. Chem. 2012, 124, 12834;
3. b) C.-X. Zhuo, C. Zheng, S.-L. You, Acc. Chem. Res. 2014, 47, 2558;
4. c) J. F. Austin, S.-G. Kim, C. J. Sinz, W.-J. Xiao, D. W. C. MacMillan, Proc. Natl. Acad. Sci. USA 2004, 101, 5482;
5. d) B. M. Trost, J. Quancard, J. Am. Chem. Soc. 2006, 128, 6314;
6. e) R. P. Reddy, H. M. L. Davies, J. Am. Chem. Soc. 2007, 129, 10312;
7. f) J. García-Fortanet, F. Kessler, S. L. Buchwald, J. Am. Chem. Soc. 2009, 131, 6676;
8. g) S. B. Jones, B. Simmons, D. W. C. MacMillan, J. Am. Chem. Soc. 2009, 131, 13606;
9. h) J. Qi, A. B. Beeler, Q. Zhang, J. A. Porco, Jr., J. Am. Chem. Soc. 2010, 132, 13642;
10. i) L. M. Repka, J. Ni, S. E. Reisman, J. Am. Chem. Soc. 2010, 132, 14418;
11. j) O. Lozano, G. Blessley, T. M. del Campo, A. L. Thompson, G. T. Giuffredi, M. Bettati, M. Walker, R. Borman, V. Gouverneur, Angew. Chem. Int. Ed. 2011, 50, 8105;
12. Angew. Chem. 2011, 123, 8255;
13. k) S. Zhu, D. W. C. MacMillan, J. Am. Chem. Soc. 2012, 134, 10815;
14. l) R. Kuwano, R. Morioka, M. Kashiwabara, N. Kameyama, Angew. Chem. Int. Ed. 2012, 51, 4136;
15. Angew. Chem. 2012, 124, 4212;
16. m) J. E. Spangler, H. M. L. Davies, J. Am. Chem. Soc. 2013, 135, 6802.
17. M. Weber, M. Weber, M. Kleine-Boymann, "Phenol" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2004.
18. a) S. K. Jackson, K.-L. Wu, T. R. R. Pettus, in Biomimetic Organic Synthesis, Wiley-VCH, Weinheim, 2011, p. 723;
19. b) S. P. Roche, J. A. Porco, Jr., Angew. Chem. Int. Ed. 2011, 50, 4068;
20. Angew. Chem. 2011, 123, 4154.
21. a) S. Quideau, L. Pouységu, D. Deffieux, Synlett 2008, 467;
22. b) L. Pouységu, D. Deffieux, S. Quideau, Tetrahedron 2010, 66, 2235;
23. c) S. Dong, J. Zhu, J. A. Porco, Jr., J. Am. Chem. Soc. 2008, 130, 2738;
24. d) T. Dohi, A. Maruyama, N. Takenaga, K. Senami, Y. Minamitsuji, H. Fujioka, S. B. Caemmerer, Y. Kita, Angew. Chem. Int. Ed. 2008, 47, 3787;
25. Angew. Chem. 2008, 120, 3847;
26. e) J. K. Boppisetti, V. B. Birman, Org. Lett. 2009, 11, 1221;
27. f) S. Quideau, G. Lyvinec, M. Marguerit, K. Bathany, A. Ozanne-Beaudenon, T. Buffeteau, D. Cavagnat, A. Chénedé, Angew. Chem. Int. Ed. 2009, 48, 4605;
28. Angew. Chem. 2009, 121, 4675;
29. g) M. Uyanik, T. Yasui, K. Ishihara, Angew. Chem. Int. Ed. 2010, 49, 2175;
30. Angew. Chem. 2010, 122, 2221;
31. h) M. Uyanik, T. Yasui, K. Ishihara, Tetrahedron 2010, 66, 5841;
32. i) T. Oguma, T. Katsuki, J. Am. Chem. Soc. 2012, 134, 20017;
33. j) T. Dohi, N. Takenaga, T. Nakae, Y. Toyoda, M. Yamasaki, M. Shiro, H. Fujioka, A. Maruyama, Y. Kita, J. Am. Chem. Soc. 2013, 135, 4558;
34. k) T. Oguma, T. Katsuki, Chem. Commun. 2014, 50, 5053.
35. a) S. Rousseaux, J. García-Fortanet, M. A. Del Aguila Sanchez, S. L. Buchwald, J. Am. Chem. Soc. 2011, 133, 9282;
36. b) T. Nemoto, Y. Ishige, M. Yoshida, Y. Kohno, M. Kanematsu, Y. Hamada, Org. Lett. 2010, 12, 5020;
37. c) M. Yoshida, T. Nemoto, Z. Zhao, Y. Ishige, Y. Hamada, Tetrahedron: Asymmetry 2012, 23, 859;
38. d) C.-X. Zhuo, S.-L. You, Angew. Chem. Int. Ed. 2013, 52, 10056;
39. Angew. Chem. 2013, 125, 10240.
40. R. J. Phipps, F. D. Toste, J. Am. Chem. Soc. 2013, 135, 1268.
41. a) V. Nair, A. T. Biju, S. C. Mathew, B. P. Babu, Chem. Asian J. 2008, 3, 810;
42. b) S. Brandes, M. Bella, A. Kjærsgaard, K. A. Jørgensen, Angew. Chem. Int. Ed. 2006, 45, 1147;
43. Angew. Chem. 2006, 118, 1165;
44. c) Z. Zhang, J. C. Antilla, Angew. Chem. Int. Ed. 2012, 51, 11778;
45. Angew. Chem. 2012, 124, 11948;
46. d) B. List, J. Am. Chem. Soc. 2002, 124, 5656;
47. e) A. Bøgevig, K. Juhl, N. Kumaragurubaran, W. Zhuang, K. A. Jørgensen, Angew. Chem. Int. Ed. 2002, 41, 1790;
48. Angew. Chem. 2002, 114, 1868;
49. f) S. Saaby, M. Bella, K. A. Jørgensen, J. Am. Chem. Soc. 2004, 126, 8120;
50. g) M. Terada, M. Nakano, H. Ube, J. Am. Chem. Soc. 2006, 128, 16044;
51. h) R. He, X. Wang, T. Hashimoto, K. Maruoka, Angew. Chem. Int. Ed. 2008, 47, 9466;
52. Angew. Chem. 2008, 120, 9608;
53. i) H. Konishi, T. Y. Lam, J. P. Malerich, V. H. Rawal, Org. Lett. 2010, 12, 2028;
54. j) C.-L. Zhu, F.-G. Zhang, W. Meng, J. Nie, D. Cahard, J.-A. Ma, Angew. Chem. Int. Ed. 2011, 50, 5869;
55. Angew. Chem. 2011, 123, 5991.
56. a) D. A. Evans, D. S. Johnson, Org. Lett. 1999, 1, 595;
57. b) K. Juhl, K. A. Jørgensen, J. Am. Chem. Soc. 2002, 124, 2420;
58. c) S. Ma, N. Jiao, Z. Zheng, Z. Ma, Z. Lu, L. Ye, Y. Deng, G. Chen, Org. Lett. 2004, 6, 2193;
59. d) S. M. Kim, H. R. Kim, D. Y. Kim, Org. Lett. 2005, 7, 2309;
60. e) L. Bernardi, W. Zhuang, K. A. Jørgensen, J. Am. Chem. Soc. 2005, 127, 5772;
61. f) R. Matsubara, S. Kobayashi, Angew. Chem. Int. Ed. 2006, 45, 7993;
62. Angew. Chem. 2006, 118, 8161;
63. g) L. Chang, Y. Kuang, B. Qin, X. Zhou, X. Liu, L. Lin, X. Feng, Org. Lett. 2010, 12, 2214;
64. h) S. Mouri, Z. Chen, H. Mitsunuma, M. Furutachi, S. Matsunaga, M. Shibasaki, J. Am. Chem. Soc. 2010, 132, 1255.
65. a) W. M. Harris, T. A. Geissman, J. Org. Chem. 1965, 30, 432;
66. b) F. Bévalot, M. Leboeuf, A. Bouquet, A. Cavé, Ann. Pharm. Fr. 1977, 35, 65;
67. c) J. T. Randolph, C. A. Flentge, P. P. Huang, D. K. Hutchinson, L. L. Klein, H. B. Lim, R. Mondal, T. Reisch, D. A. Montgomery, W. W. Jiang, S. V. Masse, L. E. Hernandez, R. F. Henry, Y. Liu, G. Koev, W. M. Kati, K. D. Stewart, D. W. A. Beno, A. Molla, D. J. Kempf, J. Med. Chem. 2009, 52, 3174.
68. a) M. Terada, Synthesis 2010, 12, 1929;
69. b) J. Yu, F. Shi, L.-Z. Gong, Acc. Chem. Res. 2011, 44, 1156;
70. c) M. Rueping, A. Kuenkel, I. Atodiresei, Chem. Soc. Rev. 2011, 40, 4539;
71. d) D. Parmar, E. Sugiono, S. Raja, M. Rueping, Chem. Rev. 2014, 114, 9047;
72. e) D. Uraguchi, M. Terada, J. Am. Chem. Soc. 2004, 126, 5356;
73. f) T. Akiyama, J. Itoh, K. Yokota, K. Fuchibe, Angew. Chem. Int. Ed. 2004, 43, 1566;
74. Angew. Chem. 2004, 116, 1592;
75. g) I. Čorić, S. Müller, B. List, J. Am. Chem. Soc. 2010, 132, 17370;
76. h) F. Xu, D. Huang, C. Han, W. Shen, X. Lin, Y. Wang, J. Org. Chem. 2010, 75, 8677;
77. i) S. Müller, M. J. Webber, B. List, J. Am. Chem. Soc. 2011, 133, 18534;
78. j) C.-H. Xing, Y.-X. Liao, J. Ng, Q.-S. Hu, J. Org. Chem. 2011, 76, 4125;
79. k) B. Xu, S.-F. Zhu, X.-L. Xie, J.-J. Shen, Q.-L. Zhou, Angew. Chem. Int. Ed. 2011, 50, 11483;
80. Angew. Chem. 2011, 123, 11685.
81. Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
82. P. Magnus, N. Garizi, K. A. Seibert, A. Ornholt, Org. Lett. 2009, 11, 5646.