Copper-catalyzed regioselective intramolecular oxidative α-functionalization of tertiary amines: An efficient synthesis of dihydro-1,3-oxazines

Angewandte Chemie - International Edition

Volumn 52, Issue 37, 2013, Pages 9791-9795

  Deb, Mohit L ^a,b   Dey, Suvendu S ^b   Bento, Isabel ^c   Barros, M Teresa ^b   Maycock, Christopher D ^a,d  

^a INSTITUTO DE TECNOLOGIA QUÍMICA E BIOLÓGICA   (Portugal)

^b UNIVERSIDADE NOVA DE LISBOA   (Portugal)

^c UNIVERSIDADE NOVA DE LISBOA   (Portugal)

^d UNIVERSITY OF LISBON   (Portugal)

Author keywords

C H activation; C O bond formation; copper catalysis; diastereoselectivity; regioselectivity

Indexed keywords

C-H ACTIVATION; C-O BOND FORMATION; COPPER CATALYSIS; DIASTEREO-SELECTIVITY; EFFICIENT SYNTHESIS; FUNCTIONALIZATIONS; REGIO-SELECTIVE; TERTIARY AMINE;

ACTIVATION ANALYSIS; CATALYSIS; COPPER; FUNCTIONAL GROUPS; REGIOSELECTIVITY; STEREOSELECTIVITY; SYNTHESIS (CHEMICAL);

AMINES;

AMINE; COPPER; NAPHTHOL DERIVATIVE; OXAZINE DERIVATIVE;

ARTICLE; C-H ACTIVATION; C-O BOND FORMATION; CATALYSIS; CHEMISTRY; COPPER CATALYSIS; CYCLOADDITION; DIASTEREOSELECTIVITY; OXIDATION REDUCTION REACTION; REGIOSELECTIVITY; STEREOISOMERISM; SYNTHESIS;

C-H ACTIVATION; C-O BOND FORMATION; COPPER CATALYSIS; DIASTEREOSELECTIVITY; REGIOSELECTIVITY;

AMINES; CATALYSIS; COPPER; CYCLOADDITION REACTION; NAPHTHOLS; OXAZINES; OXIDATION-REDUCTION; STEREOISOMERISM;

EID: 84883523381     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201304654     Document Type: Article

References (98)

1. C. S. Yeung, V. M. Dong, Chem. Rev. 2011, 111, 1215
2. M. Klussmann, D. Sureshkumar, Synthesis 2011, 353
3. W.-J. Yoo, C.-J. Li, Top. Curr. Chem. 2010, 292, 281
4. P. Anastas, N. Eghbali, Chem. Soc. Rev. 2010, 39, 301
5. C.-J. Li, Acc. Chem. Res. 2009, 42, 335
6. Z. Li, D. S. Bohle, C.-J. Li, Proc. Natl. Acad. Sci. USA 2006, 103, 8928
7. Z. Shi, F. Glorius, Angew. Chem. 2012, 124, 9354
8. Angew. Chem. Int. Ed. 2012, 51, 9220
9. C. Zhang, C. Tang, N. Jiao, Chem. Soc. Rev. 2012, 41, 3464.
10. K. R. Campos, Chem. Soc. Rev. 2007, 36, 1069
11. S.-I. Murahashi, Y. Imada, in Transition Metals for Organic Synthesis, Vol. 2, 2nd ed. (Eds.:, M. Beller, C. Bolm,), Wiley-VCH, Weinheim, 2004, pp. 497
12. X. Z. Shu, X. F. Xia, Y. F. Yang, K. G. Ji, X. Y. Liu, Y. M. Liang, J. Org. Chem. 2009, 74, 7464
13. G. Jiang, J. Chen, J. S. Huang, C. M. Che, Org. Lett. 2009, 11, 4568
14. K. M. Jones, M. Klussmann, Synlett 2012, 23, 159
15. K. Alagiri, K. R. Prabhu, Org. Biomol. Chem. 2012, 10, 835.
16. S.-I. Murahashi, D. Zhang, Chem. Soc. Rev. 2008, 37, 1490
17. A. G. Condie, J. C. Gonz'alez-Go'mez, C. R. J. Stephenson, J. Am. Chem. Soc. 2010, 132, 1464
18. M. Rueping, C. Vila, R. M. Koenigs, K. Poscharny, D. C. Fabry, Chem. Commun. 2011, 47, 2360
19. D. B. Freeman, L. Furst, A. G. Condie, C. R. J. Stephenson, Org. Lett. 2012, 14, 94.
20. W. Han, A. R. Ofial, Chem. Commun. 2009, 5024
21. W. Han, P. Mayer, A. R. Ofial, Adv. Synth. Catal. 2010, 352, 1667
22. M. Ghobrial, K. Harhammer, M. D. Mihovilovic, M. Schnurch, Chem. Commun. 2010, 46, 8836
23. H. Richter, O. G. Mancheno, Eur. J. Org. Chem. 2010, 4460
24. P. Liu, C.-Y. Zhou, S. Xiang, C.-M. Che, Chem. Commun. 2010, 46, 2739
25. C. M. R. Volla, P. Vogel, Org. Lett. 2009, 11, 1701.
26. A. J. Catino, J. M. Nichols, B. J. Nettles, M. P. Doyle, J. Am. Chem. Soc. 2006, 128, 5648.
27. S. Singhal, S. L. Jain, B. Sain, Chem. Commun. 2009, 2371
28. A. Sud, D. Sureshkumar, M. Klussmann, Chem. Commun. 2009, 3169.
29. L. Huang, X. Zhang, Y. Zhang, Org. Lett. 2009, 11, 3730
30. L. Chu, X. Zhang, F.-L. Qing, Org. Lett. 2009, 11, 2197
31. Z. Li, C.-J. Li, J. Am. Chem. Soc. 2005, 127, 3672
32. Z. Li, P. D. MacLeod, C.-J. Li, Tetrahedron: Asymmetry 2006, 17, 590
33. O. Basle, N. Borduas, P. Dubois, J. M. Chapuzet, T.-H. Chan, J. Lessard, C.-J. Li, Chem. Eur. J. 2010, 16, 8162
34. Z. Li, C.-J. Li, J. Am. Chem. Soc. 2005, 127, 6968
35. M. Niu, Z. Yin, H. Fu, Y. Jiang, Y. Zhao, J. Org. Chem. 2008, 73, 3961
36. O. Baslé, C.-J. Li, Org. Lett. 2008, 10, 3661
37. G. Zhang, Y. Zhang, R. Wang, Angew. Chem. 2011, 123, 10613
38. Angew. Chem. Int. Ed. 2011, 50, 10429.
39. E. Boess, D. Sureshkumar, A. Sud, C. Wirtz, C. Fare's, M. Klussmann, J. Am. Chem. Soc. 2011, 133, 8106
40. O. Baslé, C.-J. Li, Chem. Commun. 2009, 4124
41. E. Boess, C. Schmitz, M. Klussmann, J. Am. Chem. Soc. 2012, 134, 5317
42. A. E. King, L. M. Huffman, A. Casitas, M. Costas, X. Ribas, S. S. Stahl, J. Am. Chem. Soc. 2010, 132, 12068
43. A. E. Wendlandt, A. M. Suess, S. S. Stahl, Angew. Chem. 2011, 123, 11256
44. Angew. Chem. Int. Ed. 2011, 50, 11062.
45. L. Huang, T. Niu, J. Wu, Y. Zhang, J. Org. Chem. 2011, 76, 1759
46. M. Nishino, K. Hirano, T. Satoh, M. Miura, J. Org. Chem. 2011, 76, 6447
47. F. Yang, J. Li, J. Xie, Z.-Z. Huang, Org. Lett. 2010, 12, 5214
48. X. Ye, C. Xie, Y. Pan, L. Han, T. Xie, Org. Lett. 2010, 12, 4240
49. O. Baslé, C.-J. Li, Green Chem. 2007, 9, 1047
50. J. Chen, B. Liu, D. Liu, S. Liu, J. Cheng, Adv. Synth. Catal. 2012, 354, 2438
51. Z. Li, C.-J. Li, J. Am. Chem. Soc. 2004, 126, 11810
52. Y. Shen, Z. Tan, D. Chen, X. Feng, M. Li, C.-C. Guo, C. Zhu, Tetrahedron 2009, 65, 158.
53. P. G. Gomez, H. P. Pabon, M. A. Carvajal, J. M. Rincon, Rev. Colomb. Cienc. Quim.-Farm. 1985, 8, 15
54. K. Waisser, K. Gregor, L. Kubicova, V. Klimesova, J. Kunes, M. Machacek, J. Kaustova, Eur. J. Med. Chem. 2000, 35, 733.
55. Z. Bouaziz, J. Riondel, A. Mey, M. Berlion, J. Villard, H. Filliond, Eur. J. Med. Chem. 1991, 26, 469
56. B. A. Arthington-Skaggs, M. Motley, D. W. Warnock, C. J. Morrison, J. Clin. Microbiol. 2000, 38, 2254.
57. J. B. Chylinska, T. Urbanski, M. Mordarski, J. Med. Chem. 1963, 6, 484
58. L. Benameur, Z. Bouaziz, P. Nebois, M. H. Bartoli, M. Boitard, H. Fillion, Chem. Pharm. Bull. 1996, 44, 605.
59. B. P. Mathew, A. Kumar, S. Sharma, P. K. Shula, M. Nath, Eur. J. Med. Chem. 2010, 45, 1502
60. E. Petrlíková, K. Waisser, H. DiviŠova, P. Husaková, P. Vrabcova, J. Kuneš, K. Kolár, J. Stolariková, Bioorg. Med. Chem. 2010, 18, 8178.
61. O. S. Pedersen, E. B. Pedersen, Synthesis 2000, 479
62. A. J. Cocuzza, D. R. Chidester, B. C. Cordova, S. Jeffrey, R. L. Parsons, L. T. Bacheler, S. E. Viitanen, G. L. Trainor, S. S. Ko, Bioorg. Med. Chem. Lett. 2001, 11, 1177.
63. J. N. Joyce, S. Presgraves, L. Renish, S. Borwege, D. H. Osredkar, M. Replogle, M. PazSoldan, M. J. Millan, Exp. Neurol. 2003, 184, 393
64. P. Zhang, E. A. Terefenko, A. Fensome, Z. Zhang, Y. Zhu, J. Cohen, R. Winneker, J. Wrobel, J. Yardley, Bioorg. Med. Chem. Lett. 2002, 12, 787.
65. C. Cimarelli, G. Palmieri, E. Volpini, Tetrahedron 2001, 57, 6089
66. Y. Dong, J. Sun, X. Wang, X. Xu, L. Cao, Y. Hu, Tetrahedron: Asymmetry 2004, 15, 1667
67. X. Wang, Y. Dong, J. Sun, X. Xu, R. Li, Y. Hu, J. Org. Chem. 2005, 70, 1897
68. N. Yamazaki, T. Ito, C. Kibayashi, Org. Lett. 2000, 2, 465
69. G. Cheng, X. Wang, D. Su, H. Liu, F. Liu, Y. Hu, J. Org. Chem. 2010, 75, 1911
70. J. D. Butler, D. M. Solano, L. I. Robins, M. J. Haddadin, M. J. Kurth, J. Org. Chem. 2008, 73, 234
71. I. D. Jurberg, B. Peng, E. Wöstefeld, M. Wasserloos, N. Maulide, Angew. Chem. 2012, 124, 1986
72. Angew. Chem. Int. Ed. 2012, 51, 1950
73. J. Lu, X. Xu, S. Wang, C. Wang, Y. Hu, H. Hu, J. Chem. Soc. Perkin Trans. 1 2002, 2900.
74. W. J. Burke, J. Am. Chem. Soc. 1949, 71, 609
75. W. J. Burke, M. J. Kolbezen, C. W. Stephens, J. Am. Chem. Soc. 1952, 74, 3601
76. W. J. Burke, K. C. Murdock, G. Ec, J. Am. Chem. Soc. 1954, 76, 1677
77. W. J. Burke, R. J. Reynolds, J. Am. Chem. Soc. 1954, 76, 1291
78. W. J. Burke, C. R. Hammer, C. Weatherbee, J. Org. Chem. 1961, 26, 4403
79. D. L. Fields, J. B. Miller, D. D. Reynolds, J. Org. Chem. 1962, 27, 2749
80. A. R. Katritzky, Y.-J. Xu, R. Jain, J. Org. Chem. 2002, 67, 8234
81. W. J. Burke, C. W. Stephens, J. Am. Chem. Soc. 1952, 74, 1518
82. B. P. Mathew, M. Nath, J. Heterocycl. Chem. 2009, 46, 1003
83. Z. Tang, Z. Zhu, Z. Xia, H. Liu, J. Chen, W. Xia, X. Ou, Molecules 2012, 17, 8174
84. C.-K. Chen, A. G. Hortmann, M. R. Marzabadi, J. Am. Chem. Soc. 1988, 110, 4829
85. F. Kienzle, Tetrahedron Lett. 1983, 24, 2213
86. M. Okimoto, K. Ohashi, H. Yamamori, S. Nishikawa, M. Hoshi, T. Yoshida, Synthesis 2012, 44, 1315
87. C. L. Mathis, B. M. Gist, C. K. Frederickson, K. M. Midkiff, C. C. Marvin, Tetrahedron Lett. 2013, 54, 2101
88. J. Xuan, Z.-J. Feng, S.-W. Duan, W.-J. Xiao, RSC Adv. 2012, 2, 4065
89. G. Pandey, G. Kumaraswamy, P. Y. Reddy, Tetrahedron 1992, 48, 8295.
90. N. Cohen, J. F. Blout, R. J. Lopresti, D. P. Trullinger, J. Org. Chem. 1979, 44, 4005
91. E. M. Campl, W. R. Jackson, Q. J. McCubbin, A. E. Trnacek, J. Chem. Soc. Chem. Commun. 1994, 24, 2763
92. M. Campi, W. R. Jackson, Q. J. McCubbin, A. E. Trnacek, Aust. J. Chem. 1996, 49, 219
93. I. Azatmári, F. Fülöp, Tetrahedron Lett. 2011, 52, 4440.
94. M. Periasamy, S. Anwar, M. N. Reddy, Indian J. Chem. Sect. B 2009, 48, 1261.
95. L. Ma, W. Chen, D. Seidel, J. Am. Chem. Soc. 2012, 134, 15305.
96. A. R. Katritzky, X. Lan, Synthesis 1992, 761.
97. R. W. Van De Water, T. R. R. Pettus, Tetrahedron 2002, 58, 5367
98. A. Arduini, A. Bosi, A. Pochini, R. Ungaro, Tetrahedron 1985, 41, 3095.