Direct asymmetric dearomatization of 2-naphthols by scandium-catalyzed electrophilic amination

Angewandte Chemie - International Edition

Volumn 54, Issue 8, 2015, Pages 2356-2360

  Nan, Jiang ^a   Liu, Jingjing ^a   Zheng, Huayu ^a   Zuo, Zhijun ^a   Hou, Lei ^a   Hu, Huaiming ^a   Wang, Yaoyu ^a   Luan, Xinjun ^a  

^a NORTHWEST UNIVERSITY   (China)

Author keywords

Amination; Asymmetric catalysis; Dearomatization; Naphthol; Scandium

Indexed keywords

AMINATION; AMINES; BIOCHEMISTRY; CATALYSIS; ENANTIOSELECTIVITY; NAPHTHOL; SCANDIUM;

ASYMMETRIC CATALYSIS; AZODICARBOXYLATES; DEAROMATIZATION; ELECTROPHILIC AMINATION; ENANTIOSELECTIVE; INTERMOLECULAR REACTIONS; PHENOLIC COMPOUNDS; QUATERNARY CARBON;

AROMATIZATION;

2-NAPHTHOL; MESYLIC ACID DERIVATIVE; NAPHTHOL DERIVATIVE; SCANDIUM; TRIFLUOROMETHANESULFONIC ACID;

AMINATION; CATALYSIS; CHEMISTRY; STEREOISOMERISM;

AMINATION; CATALYSIS; MESYLATES; NAPHTHOLS; SCANDIUM; STEREOISOMERISM;

EID: 84922742711     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201409565     Document Type: Article

References (80)

1. a) J.-P. Genet, C. Greck, D. Lavergne in Modern Amination Methods (Ed.: A. Ricci), Wiley-VCH, Weinheim, 2000, chap. 3;
2. b) K. Krohn in Organic Synthesis Highlights, Wiley-VCH, Weinheim, 1991, pp. 45-53;
3. c) J. M. Janey, Angew. Chem. Int. Ed. 2005, 44, 4292;
4. Angew. Chem. 2005, 117, 4364;
5. d) A. M. R. Smith, K. K. Hii, Chem. Rev. 2011, 111, 1637.
6. a) D. A. Evans, S. G. Nelson, J. Am. Chem. Soc. 1997, 119, 6452;
7. b) K. Juhl, K. A. Jørgensen, J. Am. Chem. Soc. 2002, 124, 2420;
8. c) L. Bernardi, W. Zhuang, K. A. Jørgensen, J. Am. Chem. Soc. 2005, 127, 5772;
9. d) Y. Hasegawa, M. Watanabe, I. D. Gridnev, T. Ikariya, J. Am. Chem. Soc. 2008, 130, 2158;
10. e) T. Mashiko, N. Kumagai, M. Shibasaki, J. Am. Chem. Soc. 2009, 131, 14990;
11. f) S. Mouri, Z. Chen, H. Mitsunuma, M. Furutachi, S. Matsunaga, M. Shibasaki, J. Am. Chem. Soc. 2010, 132, 1255;
12. g) Z. Yang, Z. Wang, S. Bai, K. Shen, D. Chen, X. Liu, L. Lin, X. Feng, Chem. Eur. J. 2010, 16, 6632.
13. a) A. Bøgevig, K. Juhl, N. Kumaragurubaran, W. Zhuang, K. A. Jørgensen, Angew. Chem. Int. Ed. 2002, 41, 1790;
14. Angew. Chem. 2002, 114, 1868;
15. b) B. List, J. Am. Chem. Soc. 2002, 124, 5656;
16. c) N. Kumaragurubaran, K. Juhl, W. Zhuang, A. Bøgevig, K. A. Jørgensen, J. Am. Chem. Soc. 2002, 124, 6254;
17. d) S. Saaby, M. Bella, K. A. Jørgensen, J. Am. Chem. Soc. 2004, 126, 8120;
18. e) M. Terada, M. Nakano, H. Ube, J. Am. Chem. Soc. 2006, 128, 16044;
19. f) R. He, X. Wang, T. Hashimoto, K. Maruoka, Angew. Chem. Int. Ed. 2008, 47, 9466;
20. Angew. Chem. 2008, 120, 9608;
21. g) L. Cheng, L. Liu, D. Wang, Y.-J. Chen, Org. Lett. 2009, 11, 3874;
22. h) Z. Qian, F. Zhou, T. Du, B. Wang, M. Ding, X. Zhao, J. Zhou, Chem. Commun. 2009, 6753;
23. i) T. Bui, M. Borregan, C. F. Barbas III, J. Org. Chem. 2009, 74, 8935.
24. a) J. S. Yadav, B. V. S. Reddy, G. Rao, R. S. Veerendhar, K. Nagaiah, Chem. Lett. 2002, 318;
25. b) L. Gu, B. S. Neo, Y. Zhang, Org. Lett. 2011, 13, 1872;
26. c) S. M. Inamdar, V. K. More, S. K. Mandal, Tetrahedron Lett. 2013, 54, 530.
27. S. Brandes, M. Bella, A. Kjærsgaard, K. A. Jøgensen, Angew. Chem. Int. Ed. 2006, 45, 1147;
28. Angew. Chem. 2006, 118, 1165.
29. a) S. P. Roche, J. Porco, Jr., Angew. Chem. Int. Ed. 2011, 50, 4068;
30. Angew. Chem. 2011, 123, 4154;
31. b) C.-X. Zhuo, W. Zhang, S.-L. You, Angew. Chem. Int. Ed. 2012, 51, 12662;
32. Angew. Chem. 2012, 124, 12834;
33. c) M. Takamura, K. Funabashi, M. Kanai, M. Shibasaki, J. Am. Chem. Soc. 2000, 122, 6327;
34. d) E. Ichikawa, M. Suzuki, K. Yabu, M. Albert, M. Kanai, M. Shibasaki, J. Am. Chem. Soc. 2004, 126, 11808;
35. e) C. Y. Legault, A. B. Charette, J. Am. Chem. Soc. 2005, 127, 8966;
36. f) B. M. Trost, J. Quancard, J. Am. Chem. Soc. 2006, 128, 6314;
37. g) R. P. Reddy, H. M. L. Davies, J. Am. Chem. Soc. 2007, 129, 10312;
38. h) J. García-Fortanet, F. Kessler, S. Buchwald, J. Am. Chem. Soc. 2009, 131, 6676;
39. i) J. Qi, A. B. Beeler, Q. Zhang, J. A. Porco, Jr., J. Am. Chem. Soc. 2010, 132, 13642;
40. j) Q.-F. Wu, H. He, W.-B. Liu, S.-L. You, J. Am. Chem. Soc. 2010, 132, 11418;
41. k) Q. Cai, C. Zheng, J.-W. Zhang, S.-L. You, Angew. Chem. Int. Ed. 2011, 50, 8665;
42. Angew. Chem. 2011, 123, 8824;
43. l) Y. Fan, P. Feng, M. Liu, H. Pan, Y. Shi, Org. Lett. 2011, 13, 4494;
44. m) Q.-F. Wu, C. Zheng, S.-L. You, Angew. Chem. Int. Ed. 2012, 51, 1680;
45. Angew. Chem. 2012, 124, 1712;
46. n) J. E. Spangler, H. M. L. Davies, J. Am. Chem. Soc. 2013, 135, 6802;
47. o) H. Xiong, H. Xu, S. Liao, Z. Xie, Y. Tang, J. Am. Chem. Soc. 2013, 135, 7851;
48. p) K. V. N. Esguerra, Y. Fall, J.-P. Lumb, Angew. Chem. Int. Ed. 2014, 53, 5877;
49. Angew. Chem. 2014, 126, 5987;
50. q) B. M. Trost, V. Ehmke, B. M. O'Keefe, D. A. Bringley, J. Am. Chem. Soc. 2014, 136, 8213.
51. a) T. Nemoto, Y. Ishige, M. Yoshida, Y. Kohno, M. Kanematsu, Y. Hamada, Org. Lett. 2010, 12, 5020;
52. b) M. Yoshida, T. Nemoto, Z. Zhao, Y. Ishige, Y. Hamada, Tetrahedron: Asymmetry 2012, 23, 859;
53. c) C.-X. Zhuo, S.-L. You, Angew. Chem. Int. Ed. 2013, 52, 10056;
54. Angew. Chem. 2013, 125, 10240;
55. d) Q.-F. Wu, W.-B. Liu, C.-X. Zhuo, Z.-Q. Rong, K.-Y. Ye, S.-L. You, Angew. Chem. Int. Ed. 2011, 50, 4455;
56. Angew. Chem. 2011, 123, 4547.
57. S. Rousseaux, J. García-Fortanet, M. A. Del Aguila Sanchez, S. Buchwald, J. Am. Chem. Soc. 2011, 133, 9282.
58. a) T. Oguma, T. Katsuki, J. Am. Chem. Soc. 2012, 134, 20017;
59. b) T. Oguma, T. Katsuki, Chem. Commun. 2014, 50, 5053.
60. a) M. Uyanik, T. Yasui, K. Ishihara, Angew. Chem. Int. Ed. 2010, 49, 2175;
61. Angew. Chem. 2010, 122, 2221;
62. b) T. Dohi, N. Takenaga, T. Nakae, Y. Toyoda, M. Yamasaki, M. Shiro, H. Fujioka, A. Maruzama, Y. Kita, J. Am. Chem. Soc. 2013, 135, 4558.
63. R. J. Phipps, F. D. Toste, J. Am. Chem. Soc. 2013, 135, 1268.
64. a) J.-L. Liang, S.-X. Yuan, P. W. H. Chan, C.-M. Che, Tetrahedron Lett. 2003, 44, 5917;
65. b) J. V. Mulcahy, J. Du Bois, J. Am. Chem. Soc. 2008, 130, 12630.
66. A. Rudolph, P. H. Bos, A. Meetsma, A. Minnaard, B. L. Feringa, Angew. Chem. Int. Ed. 2011, 50, 5834;
67. Angew. Chem. 2011, 123, 5956.
68. J. Nan, Z. Zuo, L. Luo, L. Bai, H. Zheng, Y. Yuan, J. Liu, X. Luan, Y. Wang, J. Am. Chem. Soc. 2013, 135, 17306.
69. 3] to catalyze the amination of β-ketoesters with an azodicarboxylate electrophile: J. Comelles, À. Pericas, M. Moreno-Manãs, A. Vallribera, G. Drudis-Solé, A. Lledos, T. Parella, A. Roglans, S. García-Granda, L. Roces-Fernández, J. Org. Chem. 2007, 72, 2077.
70. CCDC 1024524 [(±)-9a], 1024525 [(±)-9c], 1024526 [(±)-9i], 1024527 [(±)- 9n], 1024528 [(±)-9y], 1024523 [(±)-10], and 1026471 (11) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
71. a) H. Zhang, J.-M. Yue, J. Nat. Prod. 2005, 68, 1201;
72. b) F. Li, S. S. Tartakoff, S. L. Castle, J. Am. Chem. Soc. 2009, 131, 6674;
73. c) A. R. Carroll, T. Arumugan, J. Redburn, A. Ngo, G. Guymer, P. I. Forster, R. J. Quinn, J. Nat. Prod. 2010, 73, 988;
74. d) S. B. Herzon, N. A. Calandra, S. King, Angew. Chem. Int. Ed. 2011, 50, 8863;
75. Angew. Chem. 2011, 123, 9025;
76. e) K. V. Chuang, R. Navarro, S. E. Reisman, Angew. Chem. Int. Ed. 2011, 50, 9447;
77. Angew. Chem. 2011, 123, 9619;
78. f) S. M. King, N. A. Calandra, S. B. Herzon, Angew. Chem. Int. Ed. 2013, 52, 3642;
79. Angew. Chem. 2013, 125, 3730.
80. Chiral 1,2-amino alcohols often serve as the essential building blocks for the preparation of chiral oxazoline ligands, and theunique 1,2-amino alcohol 11 might be useful in this area.