Organocatalytic enantioselective conjugate addition-cyclization domino reactions of o-N-protected aminophenyl α,β-unsaturated aldehydes

Tetrahedron Letters

Volumn 54, Issue 36, 2013, Pages 4978-4981

  Heo, Seungpyeong ^a   Kim, Shinae ^a   Kim, Sung Gon ^a  

^a Kyonggi University   (South Korea)

Author keywords

Asymmetric catalysis; Conjugate addition; Domino reaction; Organocatalysis; Tetrahydroquinoline

Indexed keywords

ALDEHYDE DERIVATIVE; AMINOPHENYL ALPHA BETA UNSATURATED ALDEHYDE; MALONIC ACID DERIVATIVE; QUINOLINE DERIVATIVE; TETRAHYDROQUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; CATALYSIS; CHEMICAL REACTION; CONJUGATE ADDITION; CYCLIZATION; DEOXYGENATION; DOMINO REACTION; ENANTIOSELECTIVITY; ORGANOCATALYSIS;

EID: 84881183562     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2013.07.031     Document Type: Article

References (85)

1. For reviews on tetrahydroquinolines, see: A.R. Katritzky, S. Rachwal, and B. Rachwal Tetrahedron 52 1996 15031
2. V. Kouznetsov, A. Palma, C. Ewert, and A. Varlamov J. Heterocycl. Chem. 35 1998 761
3. A. Mitchinson, and A. Nadin J. Chem. Soc., Perkin Trans. 1 17 2000 2862
4. Y.-G. Zhou Acc. Chem. Res. 40 2007 1357
5. V. Sridharan, P.A. Suryavanshi, and J.C. Menéndez Chem. Rev. 111 2011 7157
6. C.Z. Ding, J.T. Hunt, C. Ricca, and V. Manne Bioorg. Med. Chem. Lett. 10 2000 273
7. J.M. Urbina, J.C.G. Cortés, A. Palma, S.N. López, S.A. Zacchino, R.D. Enriz, J.C. Ribas, and V.V. Kouznetzov Bioorg. Med. Chem. 8 2000 691
8. J.-P. Liou, Z.-Y. Wu, C.-C. Kuo, C.-Y. Chang, P.-Y. Lu, C.-M. Chen, H.-P. Hsieh, and J.-Y. Chang J. Med. Chem. 51 2008 4351
9. E. Ramesh, R.D.R.S. Manian, R. Raghunathan, S. Sainath, and M. Raghunathan Bioorg. Med. Chem. 17 2009 660
10. R.T. Skerlj, G.J. Bridger, A. Kaller, E.J. McEachern, J.B. Crawford, Y. Zhou, B. Atsma, J. Langille, S. Nan, D. Veale, T. Wilson, C. Hartwig, S. Hatse, K. Princen, E. De Clercq, and D. Schols J. Med. Chem. 53 2010 3376
11. G. Dorey, B. Lockhart, P. Lestage, and P. Casara Bioorg. Med. Chem. Lett. 10 2000 935
12. S.I. Agbo, G. Hallas, and A.D. Towns Dyes Pigm. 47 2000 33
13. R. Chen, X. Yang, H. Tian, and L. Sun J. Photochem. Photobiol. A 189 2007 295
14. J.H. Rakotoson, N. Fabre, I. Jacquemond-Collet, S. Hannedouche, I. Fourasté, and C. Moulis Planta Med. 64 1998 762
15. I. Jacquemond-Collet, S. Hannedouche, N. Fabre, I. Fourasté, and C. Moulis Phytochemistry 51 1999 1167
16. M. Kusano, H. Koshino, J. Uzawa, S. Fujioka, T. Kawano, and Y. Kimura Biosci., Biotechnol., Biochem. 64 2000 2559
17. G. Schmeda-Hirschmann, E. Hormazabal, L. Astudillo, J. Rodriguez, and C. Theoduloz World J. Microbiol. Biotechnol. 21 2005 27
18. J. He, U. Lion, I. Sattler, F.A. Gollmick, S. Grabley, J. Cai, M. Meiners, H. Schünke, K. Schaumann, U. Dechert, and M. Krohn J. Nat. Prod. 68 2005 1397
19. J.A. Sikorski J. Med. Chem. 49 2006 1
20. M.E. Brousseau, E.J. Schaefer, M.L. Wolfe, L.T. Bloedon, A.G. Digenio, R.W. Clark, J.P. Mancuso, and D.J. Rader N. Eng. J. Med. 350 2004 1505
21. M. Pal Tetrahedron 65 2009 433
22. M. DePasquale, G. Cadelina, D. Knight, W. Loging, S. Winter, E. Blasi, D. Perry, and J. Keiser Drug Dev. Res. 70 2009 35
23. S. Omura, A. Nakagawa, H. Hashimoto, R. Oiwa, Y. Iwai, A. Hirano, N. Shibukawa, and Y. Kojima J. Antibiot. 33 1980 1395
24. A. Nakagawa, Y. Iwai, H. Hashimoto, N. Miyazaki, R. Oiwa, Y. Takahashi, A. Hirano, N. Shibukawa, Y. Kojima, and S. Omura J. Antibiot. 34 1981 1408
25. Y. Morimoto J. Heterocycl. Chem. 35 1998 279
26. S.-M. Lu, Y.-Q. Wang, X.-W. Han, and Y.-G. Zhou Angew. Chem., Int. Ed. 45 2006 2260
27. W.-J. Tang, S.-F. Zhu, L.-J. Xu, Q.-L. Zhou, Q.-H. Fan, H.-F. Zhou, K. Lam, and A.S.C. Chan Chem. Commun. 2007 613
28. X.-B. Wang, and Y.-G. Zhou J. Org. Chem. 73 2008 5640
29. Q.-S. Guo, D.-M. Du, and J. Xu Angew. Chem., Int. Ed. 47 2008 759
30. Z.-Y. Han, H. Xiao, X.-H. Chen, and L.-Z. Gong J. Am. Chem. Soc. 131 2009 9182
31. T. Wang, L.-G. Zhuo, Z. Li, F. Chen, Z. Ding, Y. He, Q.-H. Fan, J. Xiang, Z.-X. Yu, and A.S.C. Chan J. Am. Chem. Soc. 133 2011 9878
32. M. Rueping, A.P. Antonchick, and T. Theissmann Angew. Chem., Int. Ed. 45 2006 3683
33. S. Fustero, J. Moscardó, D. Jiménez, M.D. Pérez-Carrión, M. Sánche-Roselló, and C. del Pozo Chem. Eur. J. 14 2008 9868
34. H. Liu, G. Dagousset, G. Masson, P. Retailleau, and J. Zhu J. Am. Chem. Soc. 131 2009 4598
35. H. Xu, S.J. Zuend, M.G. Woll, Y. Tao, and E.N. Jacobsen Science 327 2010 986
36. M. Xie, X. Chen, Y. Zhu, B. Gao, L. Lin, X. Liu, and X. Feng Angew. Chem., Int. Ed. 49 2010 3799
37. Y.K. Kang, S.M. Kim, and D.Y. Kim J. Am. Chem. Soc. 132 2010 11847
38. Z.-X. Jia, Y.-C. Luo, and P.-F. Xu Org. Lett. 13 2011 832
39. K. Mori, K. Ehara, K. Kurihara, and T. Akiyama J. Am. Chem. Soc. 133 2011 6166
40. G. Dagousset, J.-P. Zhu, and G. Masson J. Am. Chem. Soc. 133 2011 14804
41. H.R. Tan, H.F. Ng, J. Chang, and J. Wang Chem. Eur. J. 18 2012 3865
42. For selected reviews on organocatalysis, see: A. Berkessel, and H. Gröger Asymmetric Organocatalysis 2005 Wiley-VCH Weinheim
43. A. Erkkilä, I. Majander, and P.M. Pihko Chem. Rev. 107 2007 5416
44. P.I. Dalko Enantioselective Organocatalysis 2007 Wiley-VCH Weinheim
45. S. Mukherjee, J.W. Yang, S. Hoffmann, and B. List Chem. Rev. 107 2007 5471
46. H. Pellisier Tetrahedron 63 2007 9267
47. A. Dondoni, and A. Massi Angew. Chem., Int. Ed. 47 2008 4638
48. S. Bertelsen, and K.A. Jørgensen Chem. Soc. Rev. 38 2009 2178
49. H. Pellissier Recent Developments in Asymmetric Organocatalysis 2010 RSC Cambridge
50. For selected reviews on organocatalytic domino reaction, see: D. Enders, C. Grondal, and M.R.M. Hüttl Angew. Chem., Int. Ed. 46 2007 1570
51. C. Grondal, M. Jeanty, and D. Enders Nat. Chem. 2 2010 167
52. Ł. Albrecht, H. Jiang, and K.A. Jørgensen Angew. Chem., Int. Ed. 50 2011 8492
53. H. Pellissier Adv. Synth. Catal. 354 2012 237
54. K.-S. Choi, and S.-G. Kim Tetrahedron Lett. 51 2010 5203
55. K.-S. Choi, and S.-G. Kim Synthesis 2010 3999
56. Y. Lee, and S.-G. Kim Bull. Korean Chem. Soc. 32 2011 311
57. S.H. Gwon, S. Kim, and S.-G. Kim Bull. Korean Chem. Soc. 32 2011 4163
58. J. Do, and S.-G. Kim Tetrahedron Lett. 52 2011 2353
59. Y. Lee, S.W. Seo, and S.-G. Kim Adv. Synth. Catal. 353 2011 2671
60. K.-S. Choi, and S.-G. Kim Eur. J. Org. Chem. 2012 1119
61. S.H. Gwon, and S.-G. Kim Bull. Korean Chem. Soc. 33 2012 2781
62. S.H. Gwon, and S.-G. Kim Tetrahedron: Asymmetry 23 2012 1251
63. S.W. Seo, and S.-G. Kim Tetrahedron Lett. 53 2012 2809
64. H. Sundén, R. Rios, I. Ibrahem, G.-L. Zhao, L. Eriksson, and A. Córdova Adv. Synth. Catal. 349 2007 827
65. H. Li, J. Wang, H. Xie, L. Zu, W. Jiang, E.N. Duesler, and W. Wang Org. Lett. 9 2007 965
66. X. Liu, and Y. Lu Org. Biomol. Chem. 8 2010 4063
67. S.-L. Zhang, H.-X. Xie, J. Zhu, H. Li, X.-S. Zhang, J. Li, and W. Wang Nat. Commun. 2 2012 211
68. For reviews on organocatalysis based on α,α-diarylprolinol O-silyl ether, see: C. Palomo, and A. Mielgo Angew. Chem., Int. Ed. 45 2006 7876
69. A. Mielgo, and C. Palomo Chem. Asian J. 3 2008 922
70. P. Melchiorre, M. Marigo, A. Carlone, and G. Bartoli Angew. Chem., Int. Ed. 47 2008 6138
71. L.-W. Xu, L. Li, and Z.-H. Shi Adv. Synth. Catal. 352 2010 243
72. K.L. Jensen, G. Dickmeiss, H. Jiang, Ł. Albrecht, and K.A. Jørgensen Acc. Chem. Res. 45 2012 248
73. For organocatalytic conjugate addition of malonates to α,β-unsaturated aldehydes, see: S. Brandau, A. Landa, J. Franzén, M. Marigo, and K.A. Jørgensen Angew. Chem., Int. Ed. 45 2006 4305
74. C. Palomo, A. Landa, A. Mielgo, M. Oiarbide, Á. Puente, and S. Vera Angew. Chem., Int. Ed. 46 2007 8431
75. Y. Wang, P. Li, X. Liang, and J. Ye Adv. Synth. Catal. 350 2008 1383
76. O.V. Maltsev, A.S. Kucherenko, and S.G. Zlotin Eur. J. Org. Chem. 2009 5134
77. I. Fleischer, and A. Pfaltz Chem. Eur. J. 16 2010 95
78. For organocatalytic conjugate addition of nitroalkanes to enones, see: Y. Wang, P. Li, X. Liang, T.Y. Zhang, and J. Ye Chem. Commun. 2008 1232
79. L. Zu, H. Xie, H. Li, J. Wang, and W. Wang Adv. Synth. Catal. 349 2007 2660
80. C. Palomo, A. Landa, A. Mielgo, M. Oiarbide, Á. Puente, and S. Vera Angew. Chem., Int. Ed. 46 2007 8431
81. H. Gotoh, H. Ishikawa, and Y. Hayashi Org. Lett. 9 2007 5307
82. L. Hojabri, A. Hartikka, and F.M. Moghaddam Adv. Synth. Catal. 349 2007 740
83. K. Mei, M. Jin, S. Zhang, P. Li, W. Liu, X. Chen, F. Xue, W. Duan, and W. Wang Org. Lett. 11 2009 2864
84. P. Li, Y. Wang, X. Liang, and J. Ye Chem. Commun. 2008 3302
85. C.E.T. Mitchell, S.E. Brenner, and S.V. Ley Chem. Commun. 2005 5346