Bifunctional cinchona alkaloids-catalyzed asymmetric [4+2] cycloaddition reaction of β,γ-unsaturated α-keto esters with oxazolones

Tetrahedron

Volumn 67, Issue 19, 2011, Pages 3337-3342

  Ying, Yin ^a   Chai, Zhuo ^b   Wang, Hai Feng ^b   Li, Peng ^b   Zheng, Chang Wu ^b   Zhao, Gang ^b   Cai, Yue Peng ^a  

^a SOUTH CHINA NORMAL UNIVERSITY   (China)

^b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

, Unsaturated keto esters; 4+2 Cycloaddition; Asymmetric catalysis; Bifunctional catalysts

Indexed keywords

CINCHONA ALKALOID; ESTER DERIVATIVE; LACTONE DERIVATIVE; OXAZOLONE;

ARTICLE; ASYMMETRIC CATALYSIS; CATALYST; CYCLOADDITION; ENANTIOSELECTIVITY; PRIORITY JOURNAL; QUANTUM YIELD; REACTION ANALYSIS; STEREOCHEMISTRY;

CINCHONA;

EID: 79954992355     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2011.03.069     Document Type: Article

References (79)

1. M.C. Elliott J. Chem. Soc., Perkin Trans. 1 2002 2301
2. P.A. Clarke, and S. Santos Eur. J. Org. Chem. 2006 2045
3. Y. Tang, J. Oppenheimer, Z.-L. Song, L.-F. You, X.-J. Zhang, and R.P. Hsung Tetrahedron 62 2006 10785
4. I. Larrosa, P. Romea, and F. Urpí Tetrahedron 64 2008 2683
5. M.G. Múnez, P. Garcíá, R.F. Mora, and D. Díez Tetrahedron 66 2010 2089
6. Organocatalyzed reactions of β,γ-unsaturated α-keto esters reported by our group, see:
7. H.-F. Wang, C.-W. Zheng, Y.-Q. Yang, Z. Chai, and G. Zhao Tetrahedron: Asymmetry 19 2008 2608
8. X.-S. Wang, C.-W. Zheng, S.-L. Zhao, Z. Chai, and G. Zhao Tetrahedron: Asymmetry 19 2008 2699
9. C.-W. Zheng, Y.-Y. Wu, X.S. Wang, and G. Zhao Adv. Synth. Catal. 350 2008 2690
10. S.-L. Zhao, C.-W. Zheng, and G. Zhao Tetrahedron: Asymmetry 20 2009 1046
11. C.-W. Zheng, Y.-W. Li, Y.-Q. Yang, H.-F. Wang, H.-F. Cui, J.-K. Zhang, and G. Zhao Adv. Synth. Catal. 351 2009 1685
12. S.-L. Zhao, C.-W. Zheng, H.-F. Wang, and G. Zhao Adv. Synth. Catal. 351 2009 2811
13. X.-K. Chen, C.-W. Zheng, S.-L. Zhao, Z. Chai, Y.-Q. Yang, G. Zhao, and W.-G. Cao Adv. Synth. Catal. 352 2010 1648
14. Organocatalyzed reactions of β,γ-unsaturated α-keto esters reported by other group, see Refs. 3-7.
15. Diels-Alder and hetero-Diels-Alder reactions:
16. D.L. Boger, and K.D. Robarge J. Org. Chem. 53 1988 3373
17. A. Sera, N. Ueda, K. Itoh, and H. Yamada Heterocycles 43 1996 2205
18. J. Thorhauge, M. Johannsen, and K.A. Jørgensen Angew. Chem., Int. Ed. 37 1998 2404
19. D.A. Evans, E.J. Olhava, J.S. Johnson, and J.M. Janey Angew. Chem., Int. Ed. 37 1998 3372
20. D.A. Evans, J.S. Johnson, and E.J. Olhava J. Am. Chem. Soc. 122 2000 1635
21. S. Leconte, G. Dujardin, and E. Brown Eur. J. Org. Chem. 2000 639
22. H. Audrain, J. Thorhauge, R.G. Hazell, and K.A. Jørgensen J. Org. Chem. 65 2000 4487
23. A. Martel, S. Leconte, G. Dujardin, E. Brown, V. Maisonneuve, and R. Retoux Eur. J. Org. Chem. 2002 514
24. A. Arbore, G. Dujardin, and C. Maignan Eur. J. Org. Chem. 2003 4118
25. K. Johl, and K.A. Jørgensen Angew. Chem., Int. Ed. 42 2003 1498
26. J. Zhou, and Y. Tang Org. Biomol. Chem. 2 2004 429
27. C. Gaulon, R. Dhal, T. Chapin, V. Maisonneuve, and G. Dujardin J. Org. Chem. 69 2004 4192
28. S. Tardy, A. Tatibouet, P. Rollin, and G. Dujardin Synlett 2006 1425
29. F. Gohier, K. Bouhadjera, D. Faye, C. Gaulon, V. Maisonneuve, G. Dujardin, and R. Dhal Org. Lett. 9 2007 211
30. G. Desimoni, G. Faita, M. Mella, F. Piccinini, and M. Toscanini Eur. J. Org. Chem. 2007 1529
31. G. Desimoni, G. Faita, M. Toscanini, and M. Boiocchi Chem. - Eur. J. 13 2007 9478
32. Friedel-Crafts reaction:
33. K.B. Jensen, J. Thorhauge, R.G. Hazell, and K.A. Jørgensen Angew. Chem., Int. Ed. 40 2001 160
34. K.A. Jørgensen Synthesis 2003 1117
35. H.L. van Lingen, W. Zhuang, T. Hansen, F.P.J.T. Rutjes, and K.A. Jørgensen Org. Biomol. Chem. 1 2003 1953
36. Y.-C. Wu, L. Liu, H.-J. Li, D. Wang, and Y.-J. Chen J. Org. Chem. 71 2006 6592
37. G. Faita, M. Mella, M. Toscanini, and G. Desimoni Tetrahedron 66 2010 3024
38. Y.-L. Liu, D.-J. Shang, X. Zhou, Y. Zhu, L.-L. Lin, X.-H. Liu, and X.-M. Feng Org. Lett. 12 2010 180
39. J. Lv, X. Li, L. Zhong, S.-Z. Luo, and J.-P. Cheng Org. Lett. 12 2010 1096
40. Michael additions and oxa-Michael additions:
41. N. Halland, T. Velgaard, and K.A. Jørgensen J. Org. Chem. 68 2003 5067
42. C. Unaleroglu, B. Temelli, and A.S. Demir Synthesis 2004 2574
43. C. Unaleroglu, S. Aytac, and B. Temelli Heterocycles 71 2007 2427
44. M. Rueping, B.J. Nachtsheim, S.A. Moreth, and M. Bolte Angew. Chem., Int. Ed. 47 2008 593
45. X. Xiong, C. Ovens, A.W. Pilling, J.W. Ward, and D.J. Dixon Org. Lett. 10 2008 565
46. R.P. Herrera, D. Monge, E. Martin-Zamora, R. Fernandez, and J.M. Lassaletta Org. Lett. 9 2007 3303
47. J.-H. Lao, X.-J. Zhang, J.-J. Wang, X.-M. Li, M. Yan, and H.-B. Luo Tetrahedron: Asymmetry 20 2009 2818
48. L. Zhou, L.-L. Lin, W.-T. Wang, J. Ji, X.-H. Liu, and X.-M. Feng Chem. Commun. 2010 3601
49. W.-J. Yao, L.-J. Pan, Y.-H. Wu, and C. Ma Org. Lett. 12 2010 2422
50. Hydrogenations:
51. Q.H. Meng, L.F. Zhu, and Z.G. Zhang J. Org. Chem. 73 2008 7209
52. M.J. Guo, D. Li, Y.H. Sun, and Z.G. Zhang Synlett 2004 741
53. Formal [3+3] annulation: C.L. Cao, X.L. Sun, Y.B. Kang, and Y. Tang Org. Lett. 9 2007 4151
54. For reviews, see:
55. R.A. Mosey, J.S. Fisk, and J.J. Tepe Tetrahedron: Asymmetry 19 2008 2755
56. N.M. Hewlett, C.D. Hupp, and J.J. Tepe Synthesis 2009 2825
57. J.S. Fisk, R.A. Mosey, and J.J. Tepe Chem. Soc. Rev. 36 2007 1432
58. M.D. Burke, and S.L. Schreiber Angew. Chem., Int. Ed. 43 2004 46
59. A.-N.R. Alba, and R. Rios Chem. Asian J. 6 2011 720 (Early View). For selected examples, see:
60. D. Seebach, G. Jaeschke, K. Gottwald, K. Matsuda, R. Formisano, and D.A. Chaplin Tetrahedron 53 1997 7539
61. J. Liang, J.C. Ruble, and G.C. Fu J. Org. Chem. 63 1998 3154
62. B.M. Trost, and X. Ariza J. Am. Chem. Soc. 121 1999 10727
63. B.M. Trost, and K. Dogra J. Am. Chem. Soc. 124 2002 7256
64. B.M. Trost, C. Jäkel, and B. Plietker J. Am. Chem. Soc. 125 2003 4438
65. A. Berkessel, F. Cleemann, S. Mukherjee, T.N. Müller, and J. Lex Angew. Chem., Int. Ed. 44 2005 807
66. S.A. Shaw, P. Aleman, J. Christy, J.W. Kampf, P. Va, and E. Vedejs J. Am. Chem. Soc. 128 2006 925
67. S. Cabrera, E. Reyes, J. Alemán, A. Milelli, S. Kobbelgaard, and K.A. Jørgensen J. Am. Chem. Soc. 130 2008 12031
68. D. Uraguchi, Y. Ueki, and T. Ooi J. Am. Chem. Soc. 130 2008 14088
69. M. Terada, H. Tanaka, and K. Sorimachi J. Am. Chem. Soc. 131 2009 3430
70. A.-N.R. Alba, X. Companyó, G. Valero, A. Moyano, and R. Rios Chem. - Eur. J. 16 2010 5354
71. X.D. Liu, L.j. Deng, X.X. Jiang, W.J. Yan, C.L. Liu, and R. Wang Org. Lett. 12 2010 876
72. X. Yang, G.J. Lu, and V.B. Birman Org. Lett. 12 2010 892
73. T. Misaki, G. Takimoto, and T. Sugimura J. Am. Chem. Soc. 132 2010 6286
74. T. Tsubogo, Y. Kano, K. Ikemoto, Y. Yamashita, and S. Kobayashi Tetrahedron: Asymmetry 21 2010 1221
75. J. Jiang, J. Qing, and L.-Z. Gong Chem. - Eur. J. 15 2009 7031
76. S.-X. Dong, X.-H. Liu, X.-H. Chen, F. Mei, Y.-L. Zhang, B. Gao, L.-L. Lin, and X.-M. Feng J. Am. Chem. Soc. 132 2010 10650
77. During the preparation of this paper, Terada also reported the reaction between β,γ-unsaturated α-keto esters and for oxazolones using axially chiral guanidine catalysts. Their system requires a low reaction temperature (-60 °C) and enantioselectivities for most substrates do not exceed 90% ee: Chem. - Eur. J. 2011, 17, 1760.
78. -3. CCDC 806009 contains the supplementary crystallographic data for 3p. These data can be obtained free of charge from the Cambridge Crystallographic Data center via www.ccdc.cam.ac.uk/data-request/cif.
79. Our results and Feng's implies that the use of bifunctional catalysts might favor the IEDDA mechanism. In Ref. 11, where guanidine was used as the catalyst, good-to-excellent diastereoselectivities were observed and the authors preferred route I based on some experimental studies.