Tuning catalysts to tune the products: Phosphine-catalyzed aza-Michael addition reaction of hydrazones with allenoates

Chemistry - An Asian Journal

Volumn 8, Issue 3, 2013, Pages 603-610

  Li, Erqing ^a   Xie, Peizhong ^a   Yang, Lihua ^a   Liang, Ling ^a   Huang, You ^a  

^a NANKAI UNIVERSITY   (China)

Author keywords

allenoates; homogeneous catalysis; hydrazones; Michael addition; phosphines

Indexed keywords

ALLENOATES; HOMOGENEOUS CATALYSIS; HYDRAZONES; MICHAEL ADDITIONS; PHOSPHINES;

CATALYSIS; CATALYSTS; PHOSPHORUS COMPOUNDS; REACTION KINETICS;

ADDITION REACTIONS;

EID: 84874239521     PISSN: 18614728     EISSN: 1861471X     Source Type: Journal    
DOI: 10.1002/asia.201201087     Document Type: Article

References (78)

1. X. Lu, C. Zhang, Z. Xu, Acc. Chem. Res. 2001, 34, 535
2. D. H. Valentine, J. H. Hillhouse, Synthesis 2003, 317
3. J. L. Methot, W. R. Roush, Adv. Synth. Catal. 2004, 346, 1035
4. X. Lu, Y. Du, C. Lu, Pure Appl. Chem. 2005, 77, 1985
5. V. Nair, R. S. Menon, A. R. Sreekanth, N. Abhilash, A. T. Biju, Acc. Chem. Res. 2006, 39, 520
6. S. E. Denmark, G. L. Beutner, Angew. Chem. 2008, 120, 1584
7. Angew. Chem. Int. Ed. 2008, 47, 1560
8. L.-W. Ye, J. Zhou, Y. Tang, Chem. Soc. Rev. 2008, 37, 1140
9. C. K.-W. Kwong, M. Y. Fu, C. S.-L. Lam, P. H. Toy, Synthesis 2008, 2307
10. C. E. Aroyan, A. Dermenci, S. J. Miller, Tetrahedron 2009, 65, 4069
11. B. J. Cowen, S. J. Miller, Chem. Soc. Rev. 2009, 38, 3102
12. A. Marinetti, A. Voituriez, Synlett 2010, 174
13. K. Beata, Cent. Eur. J. Chem. 2010, 8, 1147.
14. Y. Xia, Y. Liang, Y. Chen, M. Wang, L. Jiao, F. Huang, S. Liu, Y. Li, Z. Yu, J. Am. Chem. Soc. 2007, 129, 3470
15. X. Meng, Y. Huang, R. Chen, Org. Lett. 2009, 11, 137
16. X. Meng, Y. Huang, H. Zhao, P. Xie, J. Ma, R. Chen, Org. Lett. 2009, 11, 991
17. H. Guo, Q. Xu, O. Kwon, J. Am. Chem. Soc. 2009, 131, 6318
18. Y. Sun, X. Guan, M. Shi, Org. Lett. 2010, 12, 5664
19. T. Wang, S. Ye, Org. Lett. 2010, 12, 4168
20. X. Zhang, L. Yang, X. Tong, J. Am. Chem. Soc. 2010, 132, 2550
21. X. Chen, M. Wen, S. Ye, Z. Wang, Org. Lett. 2011, 13, 1138.
22. C. Zhang, X. Lu, J. Org. Chem. 1995, 60, 2906.
23. X. Zhu, J. Lan, O. Kwon, J. Am. Chem. Soc. 2003, 125, 4716.
24. J. Wang, M. J. Krische, Angew. Chem. 2003, 115, 6035
25. Angew. Chem. Int. Ed. 2003, 42, 5855
26. Y. S. Tran, O. Kwon, Org. Lett. 2005, 7, 4289
27. R. A. Jones, M. J. Krische, Org. Lett. 2009, 11, 1849
28. I. P. Andrews, O. Kwon, Chem. Sci. 2012, 3, 2510
29. R. A. Villa, Q. Xu, O. Kwon, Org. Lett. 2012, 14, 4634.
30. J. Szeto, V. Sriramurthy, O. Kwon, Org. Lett. 2011, 13, 5420.
31. B. M. Trost, C. Li, J. Am. Chem. Soc. 1994, 116, 3167
32. B. M. Trost, C. Li, J. Am. Chem. Soc. 1994, 116, 10819
33. B. M. Trost, G. R. Drake, J. Org. Chem. 1997, 62, 5670.
34. C. Zhang, X. Lu, Synlett 1995, 645.
35. Z. Chen, G. Zhu, Q. Jiang, D. Xiao, P. Cao, X. Zhang, J. Org. Chem. 1998, 63, 5631
36. C. Alvarez-Ibarra, A. G. Csákÿ, C. G. de La Oliva, Tetrahedron Lett. 1999, 40, 8465
37. D. Tejedor, F. García-Tellado, J. J. Marrero-Tellado, P. de Armas, Chem. Eur. J. 2003, 9, 3122
38. Y. Chung, G. C. Fu, Angew. Chem. 2009, 121, 2259
39. Angew. Chem. Int. Ed. 2009, 48, 2225
40. W. S. Smith, G. C. Fu, J. Am. Chem. Soc. 2009, 131, 14231
41. J. W. Sun, G. C. Fu, J. Am. Chem. Soc. 2010, 132, 4568.
42. T. J. Martin, V. G. Vakhshori, Y. S. Tran, O. Kwon, Org. Lett. 2011, 13, 2586
43. X. Guan, Y. Wei, M. Shi, Eur. J. Org. Chem. 2011, 2673.
44. M. Shi, Y. Wei, Z. Yuan, Eur. J. Org. Chem. 2010, 4088
45. P. Elsner, L. Bernardi, J. D. Salla, J. Overgaard, K. A. Jørgensen, J. Am. Chem. Soc. 2008, 130, 4897
46. Y. Deng, X. Jin, S. Ma, J. Org. Chem. 2007, 72, 5901
47. M. A. Silvestri, D. C. Bromfield, S. D. Lepore, J. Org. Chem. 2005, 70, 8239
48. N. Chinkov, N. Morlender-Vais, I. Marek, Tetrahedron Lett. 2002, 43, 6009
49. S. Ma, H. Xie, J. Org. Chem. 2002, 67, 6575
50. R. K. Dieter, K. Lu, S. E. Velu, J. Org. Chem. 2000, 65, 8715
51. T. Sugita, M. Eida, H. Ito, N. Komatsu, K. Abe, M. Suama, J. Org. Chem. 1987, 52, 3789.
52. S. R. Landor, The Chemistry of Allene (Ed.:, S. R. Landor,), Academic Press, New York, 1982, 2, 361
53. X. Huang, R. Shen, Synthesis 2006, 2731
54. A. Padwa, P. E. Yeske, J. Org. Chem. 1991, 56, 6386.
55. P. Xie, Y. Huang, R. Chen, Org. Lett. 2010, 12, 3768
56. X. Meng, Y. Huang, R. Chen, Chem. Eur. J. 2008, 14, 6852
57. J. Ma, P. Xie, C. Hu, Y. Huang, R. Chen, Chem. Eur. J. 2011, 17, 7418
58. P. Xie, Y. Huang, W. Lai, X. Meng, R. Chen, Org. Biomol. Chem. 2011, 9, 6707
59. P. Xie, Y. Huang, R. Chen, Chem. Eur. J. 2012, 18, 7362
60. P. Xie, W. Lai, Z. Geng, Y. Huang, R. Chen, Chem. Asian J. 2012, 7, 1533
61. C. Hu, Z. Geng, J. Ma, Y. Huang, R. Chen, Chem. Asian J. 2012, 7, 2032
62. L. Yang, P. Xie, E. Li, X. Li, Y. Huang, R. Chen, Org. Biomol. Chem. 2012, 10, 7628.
63. R. Na, C. Jing, Q. Xu, H. Jiang, X. Wu, J. Shi, J. Zhong, M. Wang, D. Benitez, E. Tkatchouk, W. Goddard III., H. Guo, O. Kwon, J. Am. Chem. Soc. 2011, 133, 13337
64. R. Na, H. Liu, Z. Li, B. Wang, J. Liu, M. Wang, M. Wang, J. Zhong, H. Guo, Tetrahedron 2012, 68, 2349.
65. N. Sokoloff, P. Latschinoff, Ber. Dtsch. Chem. Ges. 1874, 7, 1384
66. W. Heintz, N. Sokoloff, P. Latschinoff, Ber. Dtsch. Chem. Ges. 1874, 7, 1518
67. P. R. Haeseler, Org. Synth. 1926, 6, 28; for selected recent reviews on the aza-Michael reaction, see
68. D. Enders, C. Wang, J. X. Liebich, Chem. Eur. J. 2009, 15, 11058.
69. G. Zhao, M. Shi, Tetrahedron 2005, 61, 7277
70. Z. Yuan, Y. Wei, M. Shi, Eur. J. Org. Chem. 2010, 4088.
71. CCDC 906781 (3 a) and CCDC 906780 (4 g) 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.
72. M. Maire, Bull. Soc. Chim. Fr. 1908, 3, 277
73. E. E. Blaise, M. Maire, C. R. Hebd. Seances Acad. Sci. 1906, 142, 216-220
74. E. E. Blaise, M. Maire, Bull. Soc. Chim. Fr. 1908, 3, 268.
75. C. Alvarez-Ibarra, A. G. Csákÿ, C. G. de La Oliva, J. Org. Chem. 2000, 65, 3544.
76. I. C. Stewart, R. G. Bergman, F. D. Toste, J. Am. Chem. Soc. 2003, 125, 8696
77. K. Haav, J. Saame, A. Kütt, I. Leito, Eur. J. Org. Chem. 2012, 2167.
78. According to the DFT calculations, which were carried out by using the Gaussian 03 program (Gaussian 03; revision E.01, M. J. Frisch, et al., Gaussian, Inc., Wallingford, CT, 2004).