Hydrogenative dearomatization of pyridine and an asymmetric aza-Friedel-Crafts alkylation sequence

Angewandte Chemie - International Edition

Volumn 53, Issue 8, 2014, Pages 2194-2197

  Wang, Shuo Guo ^a   You, Shu Li ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

asymmetric catalysis; heterocycles; organocatalysis; reduction; synthetic methods

Indexed keywords

ASYMMETRIC CATALYSIS; DEAROMATIZATION; EFFICIENT SYNTHESIS; HETEROCYCLES; ORGANOCATALYSIS; SYNTHETIC METHODS;

FRIEDEL-CRAFTS REACTION; PYRIDINE; REACTION KINETICS; REDUCTION;

CATALYSIS;

HETEROCYCLIC COMPOUND; METAL; PHOSPHORIC ACID; PYRIDINE; PYRIDINE DERIVATIVE;

ALKYLATION; CATALYSIS; CHEMISTRY; HYDROGENATION; OXIDATION REDUCTION REACTION; STEREOISOMERISM;

ALKYLATION; AZA COMPOUNDS; CATALYSIS; HYDROGENATION; METALS; OXIDATION-REDUCTION; PHOSPHORIC ACIDS; PYRIDINES; STEREOISOMERISM;

EID: 84893848521     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201309876     Document Type: Article

References (86)

1. J. W. Daly, J. Nat. Prod. 1998, 61, 162
2. A. Mitchinson, A. Nadin, J. Chem. Soc. Perkin Trans. 1 2000, 2862
3. D. O'Hagan, Nat. Prod. Rep. 2000, 17, 435
4. P. M. Weintraub, J. S. Sabol, J. M. Kane, D. R. Borcherding, Tetrahedron 2003, 59, 2953
5. J. W. Daly, J. Med. Chem. 2003, 46, 445
6. M. G. P. Buffat, Tetrahedron 2004, 60, 1701
7. J. P. A. Harrity, O. Provoost, Org. Biomol. Chem. 2005, 3, 1349
8. J. W. Daly, T. F. Spande, H. M. Garraffo, J. Nat. Prod. 2005, 68, 1556
9. J. P. Michael, Nat. Prod. Rep. 2005, 22, 603
10. C. Escolano, M. Amat, J. Bosch, Chem. Eur. J. 2006, 12, 8198.
11. M. Rubiralta, E. Giralt, A. Diez, Piperidine: Structure, Preparation, Reactivity, and Synthetic Applications of Piperidine and its Derivatives, Elsevier, Amsterdam, 1991
12. P. D. Bailey, P. A. Millwood, P. D. Smith, Chem. Commun. 1998, 633
13. S. Laschat, T. Dickner, Synthesis 2000, 1781
14. F.-X. Felpin, J. Lebreton, Eur. J. Org. Chem. 2003, 3693
15. J. A. Bull, J. J. Mousseau, G. Pelletier, A. B. Charette, Chem. Rev. 2012, 112, 2642.
16. E. Ichikawa, M. Suzuki, K. Yabu, M. Albert, M. Kanai, M. Shibasaki, J. Am. Chem. Soc. 2004, 126, 11808
17. Z. Sun, S. Yu, Z. Ding, D. Ma, J. Am. Chem. Soc. 2007, 129, 9300
18. D. A. Black, R. E. Beveridge, B. A. Arndtsen, J. Org. Chem. 2008, 73, 1906
19. M. Á. Fernández-Ibáñez, B. Maciá, M. G. Pizzuti, A. J. Minnaard, B. L. Feringa, Angew. Chem. 2009, 121, 9503
20. Angew. Chem. Int. Ed. 2009, 48, 9339
21. N. Christian, S. Aly, K. Belyk, J. Am. Chem. Soc. 2011, 133, 2878.
22. F. Glorius, Org. Biomol. Chem. 2005, 3, 4171
23. D.-S. Wang, Q.-A. Chen, S.-M. Lu, Y.-G. Zhou, Chem. Rev. 2012, 112, 2557; For related examples, see
24. M. Studer, C. Wedemeyer-Exl, F. Spindler, H.-U. Blaser, Monatsh. Chem. 2000, 131, 1335
25. F. Glorius, N. Spielkamp, S. Holle, R. Goddard, C. W. Lehmann, Angew. Chem. 2004, 116, 2910
26. Angew. Chem. Int. Ed. 2004, 43, 2850
27. C. Y. Legault, A. B. Charette, J. Am. Chem. Soc. 2005, 127, 8966
28. X.-B. Wang, W. Zeng, Y.-G. Zhou, Tetrahedron Lett. 2008, 49, 4922
29. W.-J. Tang, J. Tan, L.-J. Xu, K.-H. Lam, Q.-H. Fan, A. S. C. Chan, Adv. Synth. Catal. 2010, 352, 1055
30. W. Tang, Y. Sun, L. Xu, T. Wang, Q. Fan, K.-H. Lam, A. S. C. Chan, Org. Biomol. Chem. 2010, 8, 3464
31. Z.-S. Ye, M.-W. Chen, Q.-A. Chen, L. Shi, Y. Duan, Y.-G. Zhou, Angew. Chem. 2012, 124, 10328
32. Angew. Chem. Int. Ed. 2012, 51, 10181.
33. H. Adolfsson, Angew. Chem. 2005, 117, 3404
34. Angew. Chem. Int. Ed. 2005, 44, 3340
35. J. Rosen, Chemtracts 2005, 18, 65
36. S.-L. You, Chem. Asian J. 2007, 2, 820
37. S. G. Ouellet, A. M. Walji, D. W. C. MacMillan, Acc. Chem. Res. 2007, 40, 1327
38. S. J. Connon, Org. Biomol. Chem. 2007, 5, 3407
39. C. Wang, X. Wu, J. Xiao, Chem. Asian J. 2008, 3, 1750
40. M. Rueping, E. Sugiono, F. R. Schoepke, Synlett 2010, 852
41. M. Rueping, J. Dufour, F. R. Schoepke, Green Chem. 2011, 13, 1084
42. C. Zheng, S.-L. You, Chem. Soc. Rev. 2012, 41, 2498; For selected examples, see
43. M. Rueping, A. P. Antonchick, Angew. Chem. 2007, 119, 4646
44. Angew. Chem. Int. Ed. 2007, 46, 4562
45. M. Rueping, A. P. Antonchick, T. Theissmann, Angew. Chem. 2006, 118, 3765
46. Angew. Chem. Int. Ed. 2006, 45, 3683
47. M. Rueping, T. Theissmann, S. Raja, J. W. Bats, Adv. Synth. Catal. 2008, 350, 1001
48. M. Rueping, T. Theissmann, Chem. Sci. 2010, 1, 473
49. M. Rueping, M. Stoeckel, E. Sugiono, T. Theissmann, Tetrahedron 2010, 66, 6565
50. M. Rueping, L. Hubener, Synlett 2011, 1243
51. M. Rueping, T. Theissmann, M. Stoeckel, A. P. Antonchick, Org. Biomol. Chem. 2011, 9, 6844
52. Q.-S. Guo, D.-M. Du, J. Xu, Angew. Chem. 2008, 120, 771
53. Angew. Chem. Int. Ed. 2008, 47, 759.
54. For a review, see:, C.-X. Zhuo, W. Zhang, S.-L. You, Angew. Chem. 2012, 124, 12834
55. Angew. Chem. Int. Ed. 2012, 51, 12662; For a cascade dearomatization of quinoline and intramolecular aza-Friedel-Crafts reaction, see
56. S.-G. Wang, W. Zhang, S.-L. You, Org. Lett. 2013, 15, 1488.
57. M. Bandini, A. Melloni, A. Umani-Ronchi, Angew. Chem. 2004, 116, 560
58. Angew. Chem. Int. Ed. 2004, 43, 550
59. T. B. Poulsen, K. A. Jørgensen, Chem. Rev. 2008, 108, 2903
60. S.-L. You, Q. Cai, M. Zeng, Chem. Soc. Rev. 2009, 38, 2190
61. M. Bandini, A. Eichholzer, Angew. Chem. 2009, 121, 9786
62. Angew. Chem. Int. Ed. 2009, 48, 9608
63. V. Terrasson, R. M. deFigueiredo, J. M. Campagne, Eur. J. Org. Chem. 2010, 2635
64. M. Zeng, S.-L. You, Synlett 2010, 1289; For selected examples on pyrrole as the nucleophile, see
65. N. A. Paras, D. W. C. MacMillan, J. Am. Chem. Soc. 2001, 123, 4370
66. W. Zhuang, N. Gathergood, R. G. Hazell, K. A. Jørgensen, J. Org. Chem. 2001, 66, 1009
67. C. Palomo, M. Oiarbide, B. G. Kardak, J. M. Garciá, A. Linden, J. Am. Chem. Soc. 2005, 127, 4154
68. D. A. Evans, K. R. Fandrick, Org. Lett. 2006, 8, 2249
69. G. Li, G. B. Rowland, E. B. Rowland, J. C. Antilla, Org. Lett. 2007, 9, 4065
70. Y.-F. Sheng, Q. Gu, A.-J. Zhang, S.-L. You, J. Org. Chem. 2009, 74, 6899
71. M. Hatano, Y. Sugiura, M. Akakura, K. Ishihara, Synlett 2011, 1247
72. C.-X. Zhuo, Q.-F. Wu, Q. Zhao, Q.-L. Xu, S.-L. You, J. Am. Chem. Soc. 2013, 135, 8169.
73. D. DellaBella, Boll. Chim. Farm. 1972, 111, 5
74. A. Gusman, F. Yuste, R. A. Toscano, J. M. Young, A. R. VanHorn, J. M. Muchowski, J. Med. Chem. 1986, 29, 589
75. A. Kleemann, J. Engel, B. Kutscher, D. Reichert, Pharmaceutical Substances, 4 th ed., Thieme, New York, 2001
76. A. R. Katritzky, R. Jain, Y.-J. Xu, P. J. Steel, J. Org. Chem. 2002, 67, 8220.
77. I. Čoric̈, S. Müller, B. List, J. Am. Chem. Soc. 2010, 132, 17370
78. F. Xu, D. Huang, C. Han, W. Shen, X. Lin, Y. Wang, J. Org. Chem. 2010, 75, 8677
79. S. Müller, M. J. Webber, B. List, J. Am. Chem. Soc. 2011, 133, 18534
80. C.-H. Xing, Y.-X. Liao, J. Ng, Q.-S. Hu, J. Org. Chem. 2011, 76, 4125
81. B. Xu, S.-F. Zhu, X.-L. Xie, J.-J. Shen, Q.-L. Zhou, Angew. Chem. 2011, 123, 11685
82. Angew. Chem. Int. Ed. 2011, 50, 11483.
83. "Naturally occurring insecticides":, I. Schmeltz, Nicotine and other tobacco alkaloids, Marcel Dekker, New York, 1971
84. H. A. Lloyd, Tetrahedron Lett. 1965, 6, 1761
85. H. A. Lloyd, Tetrahedron Lett. 1965, 6, 4537
86. M. Schaudt, S. Blechert, J. Org. Chem. 2003, 68, 2913.