Citation: Yang Lijun, Ma Junan. New Advances on Nucleophilic Phosphine-Triggered Annulation Reactions of Allenoates[J]. Acta Chimica Sinica, ;2015, 74(2): 130-148. doi: 10.6023/A15090617 shu

New Advances on Nucleophilic Phosphine-Triggered Annulation Reactions of Allenoates

Yang Lijun ,
Ma Junan ^*,,

1.
Department of Chemistry, Tianjin University and Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin 300072

Corresponding author: Ma Junan, majun_an68@tju.edu.cn
Received Date: 22 September 2015

Fund Project: the National Basic Research Program of China 973 Program,No. 2014CB745100Tianjin Municipal Science & Technology Commission No. 14JCZDJC33400the National Natural Science Foundation of China Nos. 21225208, 21532008

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In the mid 1990s, Lu and co-workers reported the nucleophilic phosphine-triggered annulation reactions of allenoates with electron-deficient olefins or imines. As one of the most efficient and straightforward synthetic strategies for the construction of highly functionalized carbocycle or heterocycle structural motifs, the development and application of nucleophilic phosphine-triggered annulation of allenoates by using various nucleophilic phosphines and electron-deficient partners have attracted more and more interests of chemists over the past decades. Furthermore, the development of asymmetric phosphine-triggered annulation of allenoates cleaved a new way to the total synthesis of bioactive natural products and medicinally important substances. In addition, aldehydes and ketones were also employed into this reaction, leading to a wide range of O-fused heterocycles. This review focuses on the important developments concerning racemic and asymmetric annulation reactions of allenoates in the past two decades.
- nucleophilic phosphine,
- allenoate,
- annulation reaction,
- Lu Reaction,
- zwitterionic intermediate
1. [1]
2. [2]
  Zhang, C.; Lu, X. J. Org. Chem. 1995, 60, 2906.
3. [3]
  Xia, Y.; Liang, Y.; Chen, Y.; Wang, M.; Jiao, L.; Huang, F.; Liu, S.; Li, Y.; Yu, Z.-X. J. Am. Chem. Soc. 2007, 129, 34701. (b) Liang, Y.; Liu, S.; Xia, Y.; Li, Y.; Yu, Z.-X. Chem. Eur. J. 2008, 14, 4361.
4. [4]
  Dudding, T.; Kwon, O.; Mercier, E. Org. Lett. 2006, 8, 3643. (b) Mercier, E.; Fonovic, B.; Henry, C.; Kwon, O.; Dudding, T. Tetrahedron Lett. 2007, 48, 3617.
5. [5]
  Xu, Z.; Lu, X. Tetrahedron Lett. 1999, 40, 549.
6. [6]
  Xu, Z.; Lu, X. Tetrahedron Lett. 1997, 38, 3461.
7. [7]
  Xu, Z.; Lu, X. J. Org. Chem. 1998, 63, 5031.
8. [8]
  Du, Y.; Lu, X.; Yu, Y. J. Org. Chem. 2002, 67, 8901.
9. [9]
  Du, Y.; Lu, X. J. Org. Chem. 2003, 68, 6463.
10. [10]
  Pyne, S. G.; Schafer, K.; Skelton, B. W.; White, A. H. Chem. Commun. 1997, 2267. (b) Ung, A. T.; Schafer, K.; Lindsay, K. B.; Pyne, S. G.; Amornraksa, K.; Wouters, R.; Van der Linden, I.; Biesmans, I.; Lesage, A. S. J.; Skelton, B. W.; White, A. H. J. Org. Chem. 2002, 67, 227.
11. [11]
  Pham, T. Q.; Pyne, S. G.; Skelton, B. W.; White, A. H. J. Org. Chem. 2005, 70, 6369. (b) Yong, S. R.; Williams, M. C.; Pyne, S. G.; Ung, A. T.; Skelton, B. W.; White, A. H.; Turner, P. Tetrahedron 2005, 61, 8120.
12. [12]
  Lu, X.; Lu, Z.; Zhang, X. Tetrahedron 2006, 62, 457.
13. [13]
  Henry, C. E.; Kwon, O. Org. Lett. 2007, 9, 3069.
14. [14]
  Lee, S. Y.; Fujiwara, Y.; Nishiguchi, A.; Kalek, M.; Fu, G. C. J. Am. Chem. Soc. 2015, 137, 4587.
15. [15]
  Guan, X.-Y.; Wei, Y.; Shi, M. Org. Lett. 2010, 12, 5024.
16. [16]
  Zou, Y.-Q.; Li, C.; Rong, J.; Yan, H.; Chen, J.-R.; Xiao, W.-J. Synlett 2011, 1000.
17. [17]
  Zhang, X.-C.; Cao, S.-H.; Wei, Y.; Shi, M. Chem. Commun. 2011, 47, 1548. (b) Zhang, X.-C.; Cao, S.-H.; Wei, Y.; Shi, M.Org. Lett. 2011, 13, 1142.
18. [18]
  Gomez, C.; Gicquel, M.; Carry, J.-C.; Schio, L.; Retailleau, P.; Voituriez, A.; Marinetti, A. J. Org. Chem. 2013, 78, 1488.
19. [19]
20. [20]
  Marco-Martinez, J.; Marcos, V.; Reboredo, S.; Filippone, S.; Martin, N. Angew. Chem., Int. Ed. 2013, 52, 5115.
21. [21]
  Kumar, K.; Kapoor, R.; Kapur, A.; Ishar, M. P. S. Org. Lett. 2000, 2, 2023.
22. [22]
23. [23]
  Jones, R. A.; Krische, M. J. Org. Lett. 2009, 11, 1849.
24. [24]
  Zhu, G.; Chen, Z.; Jiang, Q.; Xiao, D.; Cao, P.; Zhang, X. J. Am. Chem. Soc. 1997, 119, 3836.
25. [25]
  Wilson, J. E.; Fu, G. C. Angew. Chem., Int. Ed. 2006, 45, 1426.
26. [26]
  Fujiwara, Y.; Fu, G. C. J. Am. Chem. Soc. 2011, 133, 12293.
27. [27]
  Steurer, M.; Jensen, K. L.; Worgull, D.; Jorgensen, K. A. Chem. Eur. J. 2012, 18, 76.
28. [28]
  Cowen, B. J.; Miller, S. J. J. Am. Chem. Soc. 2007, 129, 10988.
29. [29]
  Voituriez, A.; Panossian, A.; Fleury-Bregeot, N.; Retailleau, P.; Marinetti, A. J. Am. Chem. Soc. 2008, 130, 14030.
30. [30]
  Voituriez, A.; Panossian, A.; Fleury-Bregeot, N.; Retailleau, P.; Marinetti, A. Adv. Synth. Catal. 2009, 351, 1968. (b) Neel, M.; Gouin, J.; Voituriez, A.; Marinetti, A. Synthesis 2011, 2003. (c) Duvvuru, D.; Pinto, N.; Gomez, C.; Betzer, J.-F.; Retailleau, P.; Voituriez, A.; Marinetti, A. Adv. Synth. Catal. 2012, 354, 408.
31. [31]
  Pinto, N.; Neel, M.; Panossian, A.; Retailleau, P.; Frison, G.; Voituriez, A.; Marinetti, A. Chem. Eur. J. 2010, 16, 1033.
32. [32]
  Schuler, M.; Voituriez, A.; Marinetti, A. Tetrahedron: Asymmetry 2010, 21, 1569. (b) Voituriez, A.; Pinto, N.; Neel, M.; Retailleau, P.; Marinetti, A. Chem. Eur. J. 2010, 16, 12541. (c) Pinto, N.; Retailleau, P.; Voituriez, A.; Marinetti, A. Chem. Commun. 2011, 47, 1015.
33. [33]
  Xiao, H.; Chai, Z.; Zheng, C.-W.; Yang, Y.-Q.; Liu, W.; Zhang, J.-K.; Zhao, G. Angew. Chem., Int. Ed. 2010, 49, 4467.
34. [34]
  Han, X.; Wang, Y.; Zhong, F.; Lu, Y. J. Am. Chem. Soc. 2011, 133, 1726.
35. [35]
  Han, X.; Wang, S.-X.; Zhong, F.; Lu, Y. Synthesis 2011, 1859.(b) Zhao, Q.; Han, X.; Wei, Y.; Shi, M.; Lu, Y. Chem. Commun. 2012, 48, 970.
36. [36]
  Zhang, X.-N.; Shi, M. ACS Catal. 2013, 3, 507.
37. [37]
  Gicquel, M.; Zhang, Y.; Aillard, P.; Retailleau, P.; Voituriez, A.; Marinetti, A. Angew. Chem., Int. Ed. 2015, 54, 5470.
38. [38]
  Tran, Y. S.; Kwon, O. J. Am. Chem. Soc. 2007, 129, 12632.
39. [39]
  Tran, Y. S.; Martin, T. J.; Kwon, O. Chem. Asian J. 2011, 6, 2101.
40. [40]
  Baskar, B.; Dakas, P.-Y.; Kumar, K. Org. Lett. 2011, 13, 1988.
41. [41]
  Li, E.; Huang, Y.; Liang, L.; Xie, P. Org. Lett. 2013, 15, 3138.
42. [42]
  Gicquel, M.; Gomez, C.; Retailleau, P.; Voituriez, A.; Marinetti, A. Org. Lett. 2013, 15, 4002.
43. [43]
  Zhong, F.; Han, X.; Wang, Y.; Lu, Y.Chem. Sci. 2012, 3, 1231.
44. [44]
  Xiao, H.; Chai, Z.; Cao, D.; Wang, H.; Chen, J.; Zhao, G. Org. Biomol. Chem. 2012, 10, 3195.
45. [45]
  Meng, W.; Zhao, H.-T.; Nie, J.; Zheng, Y.; Fu, A.; Ma, J.-A. Chem. Sci. 2012, 3, 3053.
46. [46]
  Zheng, J.; Huang, Y.; Li, Z. Org. Lett. 2013, 15, 5064.
47. [47]
  Li, E.; Huang, Y. Chem. Commun. 2014, 50, 948.
48. [48]
  Li, E.; Jia, P.; Liang, L.; Huang, Y. ACS Catal. 2014, 4, 600. (b) Li, E.; Huang, Y. Chem. Eur. J. 2014, 20, 3520.
49. [49]
  Zhu, X.-F.; Henry, C. E.; Kwon, O. Tetrahedron 2005, 61, 6276.
50. [50]
  Zhao, G.-L.; Shi, M. J. Org. Chem. 2005, 70, 9975.
51. [51]
  Tang, X.; Zhang, B.; He, Z.; Gao, R.; He, Z. Adv. Synth. Catal. 2007, 349, 2007.
52. [52]
  Zhang, B.; He, Z.; Xu, S.; Wu, G.; He, Z. Tetrahedron 2008, 64, 9471.
53. [53]
  Wang, Y.-Q.; Zhang, Y.; Dong, H.; Zhang, J.; Zhao, J. Eur. J. Org. Chem. 2013, 3764.
54. [54]
  Chen, X.-Y.; Lin, R.-C.; Ye, S. Chem. Commun. 2012, 48, 1317.
55. [55]
  Yang, L.-J.; Wang, S.; Nie, J.; Li, S.; Ma, J.-A. Org. Lett. 2013, 15, 5214. (b) Yang, L.-J.; Li, S.; Wang, S.; Nie, J.; Ma, J.-A. J. Org. Chem. 2014, 79, 3547.
56. [56]
  Jean, L.; Marinetti, A. Tetrahedron Lett. 2006, 47, 2141.
57. [57]
  Fleury-Bregeot, N.; Jean, L.; Retailleau, P.; Marinetti, A. Tetrahedron 2007, 63, 11920.
58. [58]
59. [59]
60. [60]
  Scherer, A.; Gladysz, J. A. Tetrahedron Lett. 2006, 47, 6335.
61. [61]
  Fang, Y.-Q.; Jacobsen, E. N. J. Am. Chem. Soc. 2008, 130, 5660.
62. [62]
  Han, X.; Zhong, F.; Wang, Y.; Lu, Y. Angew. Chem., Int. Ed. 2012, 51, 767.
63. [63]
  Henry, C. E.; Xu, Q.; Fan, Y.-C.; Martin, T. J.; Belding, L.; Dudding, T.; Kwon, O. J. Am. Chem. Soc. 2014, 136, 11890.
64. [64]
  Andrews, I. P.; Kwon, O. Chem. Sci. 2012, 3, 2510.
65. [65]
  Zhu, X.-F.; Lan, J.; Kwon, O. J. Am. Chem. Soc. 2003, 125, 4716.
66. [66]
  Tran, Y. S.; Kwon, O. Org. Lett. 2005, 7, 4289. (b) Villa,R. A.; Xu,Q.; Kwon, O. Org. Lett. 2012, 14, 4634.
67. [67]
  Castellano, S.; Fiji, H. D. G.; Kinderman, S. S.; Watanabe, M.; Leon, P.; Tamanoi, F.; Kwon, O. J. Am. Chem. Soc. 2007, 129, 5843. (b) Cruz, D.; Wang, Z.; Kibbie, J.; Modlin, R.; Kwon, O. Proc. Natl. Acad. Sci. U. S. A. 2011, 108, 6769.
68. [68]
  Chen, X.-Y.; Ye, S. Eur. J. Org. Chem. 2012, 5723.
69. [69]
  Takizawa, S.; Arteaga, F. A.; Yoshida, Y.; Suzuki, M.; Sasai, H. Asian J. Org. Chem. 2014, 3, 412.
70. [70]
  Wurz, R. P.; Fu,G. C. J. Am. Chem. Soc. 2005, 127, 12234.
71. [71]
  Xiao, H.; Chai, Z.; Wang, H.-F.; Wang, X.-W.; Cao, D.-D.; Liu, W.; Lu, Y.-P.; Yang, Y.-Q.; Zhao, G. Chem. Eur. J. 2011, 17, 10562.
72. [72]
  Na, R.; Jing, C.; Xu, Q.; Jiang, H.; Wu, X.; Shi, J.; Zhong, J.; Wang, M.; Benitez, D.; Tkatchouk, E.; Goddard III, W. A.; Guo, H.; Kwon, O. J. Am. Chem. Soc. 2011, 133, 13337.
73. [73]
  Wang, D.; Lei, Y.; Wei, Y.; Shi, M. Chem. Eur. J. 2014, 20, 15325.
74. [74]
  Meng, X.; Huang, Y.; Chen, R. Org. Lett. 2009, 11, 137.
75. [75]
  Meng, X.; Huang, Y.; Zhao, H.; Xie, P.; Ma, J.; Chen, R. Org. Lett. 2009, 11, 991.
76. [76]
  Sun, Y.-W.; Guan, X.-Y.; Shi, M. Org. Lett. 2010, 12, 5664.
77. [77]
  Xu, S.; Zhou, L.; Ma, R.; Song, H.; He, Z. Org. Lett. 2010, 12, 544.
78. [78]
  Xu, S.; Zhou, L.; Ma, R.; Song, H.; He, Z. Chem. Eur. J. 2009, 15, 8698.
79. [79]
  Wang, T.; Ye, S. Org. Biomol. Chem. 2011, 9, 5260.
80. [80]
  Zhu, X.-F.; Henry, C. E.; Wang, J.; Dudding, T.; Kwon, O. Org. Lett. 2005, 7, 1387.
81. [81]
  Zhu, X.-F.; Schaffner, A.-P.; Li, R. C.; Kwon, O. Org. Lett. 2005, 7, 2977.
82. [82]
  Creech, G. S.; Kwon, O. Org. Lett. 2008, 10, 429.
83. [83]
  Wang, T.; Ye, S. Org. Lett. 2010, 12, 4168.
84. [84]
  Kumar, K.; Kapur, A.; Ishar, M. P. S. Org. Lett. 2000, 2, 787.
85. [85]
  Lu, Z.; Zheng, S.; Zhang, X.; Lu, X. Org. Lett. 2008, 10, 3267.
86. [86]
  Zhang, Q.;Yang, L.; Tong, X. J. Am. Chem. Soc. 2010, 132, 2550.
87. [87]
  Gu, Y.; Hu, P.; Ni, C.; Tong, X. J. Am. Chem. Soc. 2015, 137, 6400.
88. [88]
  Han, X.; Yao, W.; Wang, T.; Tan, Y. R.; Yan, Z.; Kwiatkowski, J.; Lu, Y. Angew. Chem., Int. Ed. 2014, 53, 5643.
89. [89]
  Ziegler, D. T.; Riesgo, L.; Ikeda, T.; Fujiwara, Y.; Fu, G. C. Angew. Chem.,Int. Ed. 2014, 53, 13183.
90. [90]
  Kramer, S.; Fu, G. C. J. Am. Chem. Soc. 2015, 137, 3803.
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