A Phosphine-Catalyzed Novel Asymmetric [3+2] Cycloaddition of C,N-Cyclic Azomethine Imines with δ-Substituted Allenoates

Chemistry - A European Journal

Volumn 20, Issue 47, 2014, Pages 15325-15329

  Wang, De ^a   Lei, Yu ^a   Wei, Yin ^a   Shi, Min ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

azomethine imines; chiral phosphine; cycloaddition; enantioselectivity; substituted allenoates

Indexed keywords

CYCLOADDITION; ENANTIOSELECTIVITY; PHOSPHORUS COMPOUNDS;

ASYMMETRIC SYNTHESIS; ASYMMETRIC [3+2] CYCLOADDITION; AZOMETHINE; C-C BOND FORMATION; CHIRAL PHOSPHINE; CYCLOADDITIONS; SUBSTITUTED ALLENOATES; TETRAHYDROQUINOLINE;

NITROGEN COMPOUNDS;

EID: 84941117896     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201405191     Document Type: Article

References (89)

1. C. Zhang, X. Lu, J. Org. Chem. 1995, 60, 2906.
2. P. I. Dalko, Comprehensive Enantioselective Organocatalysis: Catalysts, Reactions, and Applications, Wiley-VCH, Weinheim, 2013. For reviews on phosphine-catalyzed reactions, see:
3. X. Lu, C. Zhang, Z. Xu, Acc. Chem. Res. 2001, 34, 535;
4. J. L. Methot, W. R. Roush, Adv. Synth. Catal. 2004, 346, 1035;
5. L.-W. Ye, J. Zhou, Y. Tang, Chem. Soc. Rev. 2008, 37, 1140;
6. B. J. Cowen, S. J. Miller, Chem. Soc. Rev. 2009, 38, 3102;
7. A. Marinetti, A. Voituriez, Synlett 2010, 174;
8. Y. Wei, M, Shi, Acc. Chem. Res. 2010, 43, 1005;
9. S.-X. Wang, X. Han, F. Zhong, Y. Lu, Synlett 2011, 19, 2766;
10. Q.-Y. Zhao, Z. Lian, Y. Wei, M. Shi, Chem. Commun. 2012, 48, 1724;
11. C. Nising, S. Bräse, Chem. Soc. Rev. 2008, 37, 1218;
12. Y.-C. Fan, O. Kwon, Chem. Commun. 2013, 49, 11588;
13. Z. Wang, X. Xu, O. Kwon, Chem. Soc. Rev. 2014, 43, 2927;
14. A. Moyano, R. Rios, Chem. Rev. 2011, 111, 4703.
15. X.-F. Zhu, C. E. Henry, J. Wang, T. Dudding, O. Kwon, Org. Lett. 2005, 7, 1387;
16. X.-F. Zhu, A.-P. Schaffner, R. C. Li, O. Kwon, Org. Lett. 2005, 7, 2977;
17. T. Dudding, O. Kwon, E. Mercier, Org. Lett. 2006, 8, 3643;
18. G. S. Creech, O. Kwon, Org. Lett. 2008, 10, 429;
19. X.-F. Zhu, C.-E. Henry, O. Kwon, J. Am. Chem. Soc. 2007, 129, 6722;
20. Y. S. Tran, O. Kwon, J. Am. Chem. Soc. 2007, 129, 12632;
21. R. Na, C. Jing, Q. Xu, H. Jiang, X. Wu, J. Shi, J. Zhong, M. Wang, D. Benitez, E. Tkatchouk, W. A. Goddard III, H. Guo, O. Kwon, J. Am. Chem. Soc. 2011, 133, 13337;
22. C. Jing, R. Na, B. Wang, H. Liu, L. Zhang, J. Liu, M. Wang, J. Zhong, O. Kwon, H. Guo, Adv. Synth. Catal. 2012, 354, 1023;
23. C. E. Henry, Q. Xu, Y. C. Fan, T. J. Martin, L. Belding, T. Dudding, O. Kwon, J. Am. Chem. Soc. 2014, 136, 11890.
24. X. Meng, Y. Huang, H. Zhao, P. Xie, J. Ma, R. Chen, Org. Lett. 2009, 11, 911;
25. R. Ma, S. Xu, X. Tang, G. Wu, Z. He, Tetrahedron 2011, 67, 103;
26. S. Xu, L. Zhou, R. Ma, H. Song, Z. He, Chem. Eur. J. 2009, 15, 8698;
27. A. Jose, K. C. S. Lakshmi, E. Suresh, V. Nair, Org. Lett. 2013, 15, 1858;
28. C. Gomez, M. Gicquel, J.-C. Carry, L. Schio, P. Retailleau, A. Voituriez, A. Marinetti, J. Org. Chem. 2013, 78, 1488;
29. B. S. Santos, T. M. V. D. Pinho e Melo, Eur. J. Org. Chem. 2013, 3901;
30. W. Meng, H.-T. Zhao, J. Nie, Y. Zheng, A. Fuc, J.-A Ma, Chem. Sci. 2012, 3, 3053;
31. J. Marco-Martínez, V. Marcos, S. Reboredo, S. Filippone, N. Martín, Angew. Chem. Int. Ed. 2013, 52, 5115;
32. Angew. Chem. 2013, 125, 5219;
33. M. Steurer, K. L. Jensen, D. Worgull, K. A. Jørgensen, Chem. Eur. J. 2012, 18, 76.
34. G. Zhu, Z. Chen, Q. Jiang, D. Xiao, P. Cao, X. Zhang, J. Am. Chem. Soc. 1997, 119, 3836.
35. J. E. Wilson, G. C. Fu, Angew. Chem. Int. Ed. 2006, 45, 1426;
36. Angew. Chem. 2006, 118, 1454;
37. Y. K. Chung, G. C. Fu, Angew. Chem. Int. Ed. 2009, 48, 2225;
38. Angew. Chem. 2009, 121, 2259;
39. R. P. Wurz, G. C. Fu, J. Am. Chem. Soc. 2005, 127, 12234;
40. Y. Fujiwara, G. C. Fu, J. Am. Chem. Soc. 2011, 133, 12293.
41. L. Jean, A. Marinetti, Tetrahedron Lett. 2006, 47, 2141;
42. N. Fleury-Brégeot, L. Jean, P. Retailleau, A. Marinetti, Tetrahedron 2007, 63, 11920;
43. A. Panossian, N. Fleury-Brégeot, A. Marinetti, Eur. J. Org. Chem. 2008, 3826;
44. N. Pinto, N. Fleury-Brégeot, A. Marinetti, Eur. J. Org. Chem. 2009, 146;
45. A. Voituriez, A. Panossian, N. Fleury-Brégeot, P. Retailleau, A. Marinetti, J. Am. Chem. Soc. 2008, 130, 14030;
46. A. Voituriez, A. Panossian, N. Fleury-Brégeot, P. Retailleau, A. Marinetti, Adv. Synth. Catal. 2009, 351, 1968;
47. N. Pinto, M. Neel, A. Panossian, P. Retailleau, G. Frison, A. Voituriez, A. Marinetti, Chem. Eur. J. 2010, 16, 1033;
48. A. Voituriez, N. Pinto, M. Neel, P. Retailleau, A. Marinetti, Chem. Eur. J. 2010, 16, 12541;
49. M. Schuler, A. Voituriez, A. Marinetti, Tetrahedron: Asymmetry 2010, 21, 1569;
50. N. Pinto, P. Retailleau, A. Voituriez, A. Marinetti, Chem. Commun. 2011, 47, 1015;
51. M. Neel, J. Gouin, A. Voituriez, A. Marinetti, Synthesis 2011, 12, 2003;
52. D. Duvvuru, N. Pinto, C. Gomez, J.-F. Betzer, P. Retailleau, A. Voituriez, A. Marinetti, Adv. Synth. Catal. 2012, 354, 408.
53. B. J. Cowen, S. J. Miller, J. Am. Chem. Soc. 2007, 129, 10988;
54. Y.-Q. Fang, E. N. Jacobsen, J. Am. Chem. Soc. 2008, 130, 5660;
55. H. Xiao, Z. Chai, C.-W. Zheng, Y.-Q. Yang, W. Liu, J.-K. Zhang, G. Zhao, Angew. Chem. Int. Ed. 2010, 49, 4467;
56. Angew. Chem. 2010, 122, 4569;
57. X. Han, Y. Wang, F. Zhong, Y. Lu, J. Am. Chem. Soc. 2011, 133, 1726;
58. X. Han, S.-X. Wang, F. Zhong, Y. Lu, Synthesis 2011, 12, 1859.
59. D. J. Wallace, R. L. Sidda, R. A. Reamer, J. Org. Chem. 2007, 72, 1051;
60. M. Sampath, T.-P. Loh, Chem. Commun. 2009, 1568;
61. M. Sampath, T.-P. Loh, Chem. Sci. 2010, 1, 739.
62. E. Li, Y. Huang, L. Liang, P. Xie, Org. Lett. 2013, 15, 3138;
63. M. Gicquel, C. Gomez, P. Retailleau, A. Voituriez, A. Marinetti, Org. Lett. 2013, 15, 4002;
64. E. Li, Y. Huang, Chem. Commun. 2014, 50, 948.
65. G.-L. Zhao, J.-W. Huang, M. Shi, Org. Lett. 2003, 5, 4737;
66. Y.-L. Shi, M. Shi, Org. Lett. 2005, 7, 3057;
67. X.-C. Zhang, S.-H. Cao, Y. Wei, M. Shi, Chem. Commun. 2011, 47, 1548;
68. X.-C. Zhang, S.-H. Cao, Y. Wei, M. Shi, Org. Lett. 2011, 13, 1142;
69. D. Wang, Y. Wei, M. Shi, Chem. Commun. 2012, 48, 2764;
70. Q.-Y. Zhao, C.-K. Pei, X.-Y. Guan, M. Shi, Adv. Synth. Catal. 2011, 353, 1973;
71. C.-K. Pei, Y. Jiang, Y. Wei, M. Shi, Angew. Chem. Int. Ed. 2012, 51, 11328;
72. Angew. Chem. 2012, 124, 11490.
73. T. Hashimoto, Y. Maeda, M. Omote, H. Nakatsu, K. Maruoka, J. Am. Chem. Soc. 2010, 132, 4076;
74. T. Hashimoto, M. Omote, K. Maruoka, Angew. Chem. Int. Ed. 2011, 50, 3489;
75. Angew. Chem. 2011, 123, 3551;
76. T. Hashimoto, M. Omote, K. Maruoka, Angew. Chem. Int. Ed. 2011, 50, 8952;
77. Angew. Chem. 2011, 123, 9114;
78. D. Wang, H.-P. Deng, Y. Wei, Q. Xu, M. Shi, Eur. J. Org. Chem. 2013, 401;
79. Z. Li, H. Yu, H. Liu, L. Zhang, H. Jiang, B. Wang, H. Guo, Chem. Eur. J. 2014, 20, 1731.
80. J. D. Scott, R. M. Williams, Chem. Rev. 2002, 102, 1669;
81. K. W. Bentley, Nat. Prod. Rep. 2004, 21, 395;
82. K. W. Bentley, Nat. Prod. Rep. 2005, 22, 249;
83. K. W. Bentley, Nat. Prod. Rep. 2006, 23, 444.
84. D. Liu, W. Li, X. Zhang, Org. Lett. 2002, 4, 4471;
85. W. Zhang, Y. Chi, X. Zhang, Acc. Chem. Res. 2007, 40, 1278.
86. Y. Liang, S. Liu, Y. Xia, Y. Li, Z.-X. Yu, Chem. Eur. J. 2008, 14, 4361;
87. Y. Xia, Y. Liang, Y. Chen, M. Wang, L. Jiao, F. Huang, S. Liu, Y. Li, Z.-X. Yu, J. Am. Chem. Soc. 2007, 129, 3470;
88. Y. Liang, S. Liu, Z.-X. Yu, Synlett 2009, 905.
89. 2O influenced proton transfer, see ref. [16b].