Citation: Zhao Wenxian, Yang Daiyue, Zhang Yuhua. Progress in Efficient Chiral Phosphine Ligand[J]. Chinese Journal of Organic Chemistry, ;2016, 36(10): 2301-2316. doi: 10.6023/cjoc201603006 shu

Progress in Efficient Chiral Phosphine Ligand

  • Corresponding author: Zhao Wenxian, zhwx2595126@163.com
  • Received Date: 4 March 2016
    Revised Date: 30 May 2016

    Fund Project: Project supported by the National Natural Science Foundation of China Nos.20972091, 21172139the Key Science Research of Education Committee in Henan Province No.16A150020

Figures(19)

  • Synthesis and application of chiral phosphine ligand is an important research area in the field of asymmetric synthesis. According to the chiral center and the structural characteristics, the recent development of efficient chiral phosphine ligand in asymmetric synthesis is reviewed, and the prospects of chiral phosphine ligand are also discussed.
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    1. [1]

      Knowles, W. S.; Sabacky, M. J. J. Chem. Soc., Chem. Commun. 1968, 20, 1445.

    2. [2]

      Horner, L.; Sieged, H.; Buthe, H. Angew. Chem., Int. Ed. Engl. 1968, 7, 942.

    3. [3]

      Knowles, W. S.; Sabacky, M. J. US 3849480, 1968[Chem. Abstr. 1971, 82, 86086].

    4. [4]

      William, H. P.; Minn, C. C. J. Org. Chem. 1987, 52, 3176. 

    5. [5]

      Noyori, R. Science 1990, 248, 1194.

    6. [6]

      Parshall, G. W.; Nugent, W. A. CHEMTECH 1988, 18, 376.

    7. [7]

      Hayashi, T.; Katsumura, A.; Konishi, M.; Kumada, M. Tetrahedron Lett. 1979, 20, 425.

    8. [8]

      Kagan, H. B. Adv. Catal. 1986, 25, 88.

    9. [9]

      Uozumi, Y.; Hayashi, T. J. Am. Chem. Soc. 1991, 113, 9887. 

    10. [10]

      Kitayama, K.; Tsuji, H.; Uozumi, Y.; Hayashi, T. Tetrahedron Lett. 1996, 37, 4169.

    11. [11]

      Farkas, G.; Balogh, S.; Szollosy, A.; Uerge, L.; Darvas, F.; Bakos, J. Tetrahedron:Asymmetry 2011, 22, 2104.

    12. [12]

      Urbaneja, X.; Mercier, A.; Besnard, C.; Kündig, E. P. Chem. Commun. 2011, 47, 3739. 

    13. [13]

      Li, W. G.; Zhang, Z. G.; Xiao, D. M.; Zhang, X. M. J. Org. Chem. 2000, 65, 3489. 

    14. [14]

      Zhang, W. C.; Zhang, X. M. J. Org. Chem. 2007, 72, 1020. 

    15. [15]

      He, H.; Zheng. X. J.; You, S. L. Org. Lett. 2007, 9, 4339. (b) Liu, W. B.; He, H.; You, S. L. Org. Lett. 2008, 10, 1815. (c) Xu, Q. L.; Dai, L. X.; You, S. L. Org. Lett. 2009, 12, 800. (d) Xu, Q. L.; Dai, L. X.; You, S. L. Org. Lett. 2012, 14, 2579. 

    16. [16]

      Xu, Q. L.; Liu, Q. L.; Dai, L. X.; You, S. L. J. Org. Chem. 2010, 75, 4615. (b) Wu, Q. F.; He, H.; You, S. L.; Liu, W. B. J. Am. Chem. Soc. 2010, 132, 11418. (c) Zhou, C. X.; Zheng, C.; You, S. L. Acc. Chem. Res. 2014, 47, 2558. (d) Yang, Z. P.; Wu, Q. F.; You, S. L. J. Am. Chem. Soc. 2015, 135, 15899. 

    17. [17]

      Li, K.; Hu, N.; Luo, R. S.; Yuan, W. C.; Tang, W. J. J. Org. Chem. 2013, 78, 6350. 

    18. [18]

      Yang, X. T.; Xu, G. Q.; Tang, W. J. Tetrahedron 2016, 72, 5178. (b) Du, K.; Guo, P.; Chen, Y.; Tang, W. J. Angew. Chem., Int. Ed. 2015, 54, 3033. 

    19. [19]

      Hu, N. F.; Li, K.; Wang, Z.; Tang, W. J. Angew. Chem., Int. Ed. 2016, 55, 1. 

    20. [20]

    21. [21]

      Burk, M. J.; Tharper, G. P.; Christopher, S. J. Am. Chem. Soc. 1995, 117, 4423. 

    22. [22]

      Imamoto, T.; Watanabe, T.; Wada, Y.; Masuda, H.;Yamada, H.; Tsuruta, H.; Matsukawa, S.; Yamaguchi, K. J. Am. Chem. Soc. 1998, 120, 1635. 

    23. [23]

      Imamoto, T.; Tamura, K.; Zhang, Z. F.; Horiuchi, Y. Sugiya, M.; Yoshida, K.; Yanagisawa, A.; Gridnev, L. D. J. Am. Chem. Soc. 2011, 133, 1754. 

    24. [24]

      Zhang, Z.; Tamura, K.; Mayama, D.; Sugiya, M.; Imamoto, T. J. Org. Chem. 2012, 77, 4184. 

    25. [25]

      Geng, H. L.; Huang, K. X.; Sun, T.; Li, W.; Zhang, X. W.; Wu, W. J.; Zhang. X. M. J. Org. Chem. 2011, 76, 332. (b) Huang, K. X.; Zhang, X. W.; Geng. H. L.; Li, S. K.; Zhang, X. M. ACS Catal. 2012, 2, 1343. (c) Jiang, J.; Liu, W. X.; Lv, H.; Zhang, X. M. Org. Lett. 2015, 17, 1154.

    26. [26]

      Tang, W. J.; Qu, B.; Andrew, G.; Chris, H.; Rodriguez, S.; Wei, X. D.; Haddad, N.; Narayanan, B.; Ma, S. L. Org. Lett. 2010, 12, 176. 

    27. [27]

      Liu, G. D.; Liu, X. Q.; Cai, Z. H.; Tang, W. J. Angew. Chem., Int. Ed. 2013, 52, 4235. (b) Luo, R. S.; Li, K.; Hu, Y. L.; Jiao, G. J.; Xu, G. P.; Tang, W. J. Adv. Synth. Catal. 2013, 355, 1297. 

    28. [28]

      Huang, L. W.; Zhu, J. B.; Jiao, G. J.; Wang, Z.; Yu, X. X.; Deng, W. P.; Tang, W. J. Angew. Chem., Int. Ed. 2016, 55, 4527. 

    29. [29]

      Morrison, J. D.; Masler, W. F. J. Org. Chem. 1974, 39, 270. 

    30. [30]

      Morison, J. D.; Burnett, R. E. Aguiar, A. M.; Morrow, C. J.; Phillips, C. J. Am. Chem. Soc. 1971, 93, 1301. 

    31. [31]

      Dawson, G. J.; Frost, C. G.; Williams, J. M. J.; Coote, S. J. Tetrahedron Lett. 1993, 34, 3149. 

    32. [32]

      Sprinz, J.; Helmechen, G. Tetrahedron Lett. 1993, 34, 1769. 

    33. [33]

      Janssen, J. P.; Helmechen, G. Tetrahedron Lett. 1997, 38, 8025. 

    34. [34]

    35. [35]

      Pasquier, C.; Naili, S.; Pelinski, L.; Brocard, J.; Mortreux, A.; Agbossou, F. Tetrahedron:Asymmetry 1998, 9, 193.

    36. [36]

      Hamada, Y.; Seto, N.; Ohmori, H.; Hatano, K. Tetrahedron Lett. 1996, 37, 7565.

    37. [37]

      Chen, Z. G.; Jiang, Q. Z.; Zhu, G. X.;Xiao, D. M.; Cao, P.; Guo, C.; Zhang, X. M. J. Org. Chem. 1997, 62, 4521. 

    38. [38]

      Zhu, G. X.; Chen, Z. G.; Jiang, Q. Z. J. Am. Chem. Soc. 1997, 119, 3836. 

    39. [39]

      Miyashita, A.; Yasuda, A.; Takaya, H.; Toriumi, K.; Ito, T.; Noyori, R. J. Am. Chem. Soc. 1980, 102, 7932. 

    40. [40]

      Yang, H.; Alvarez-Gressier, M.; Lugan, N.; Mathieu, R. Organometallics 1997, 16, 1401.

    41. [41]

      Okda, T.; Morito, T.; Achiwa, K. Chem. Lett. 1990, 16, 999.

    42. [42]

    43. [43]

      Hayashi, T.; Konishi, M.; Fukushima, M. Bull. Soc. Chim. Belg. 1979, 11, 923.

    44. [44]

      Meek, D. W. In Homogeneous Catalysis with Metal Phosphine Complexes, Plenum Press, New York, 1983, Chapter 8.

    45. [45]

      Dang, T. P.; Kagan, H. B. J. Chem. Soc. 1971, 93, 484;

    46. [46]

      Henri, B. K. J. Am. Chem. Soc. 1972, 94, 6429. 

    47. [47]

      Brown, J. M.; Murrer, B. A. Tetrahedron Lett. 1980, 21, 581. 

    48. [48]

      Towsend, J. M.; Blount, J. F.; Sun, R. C.; Zawoiski, S.; ValentineJr, D. J. Org. Chem. 1980, 45, 2995. 

    49. [49]

      Yamagishi, T.; Yatagai, M.; Hatakeyama, H.; Hida, M. Bull. Chem. Soc. Jpn. 1984, 57, 1897. 

    50. [50]

      Morimoto, T.; Chiba, M.; Achiwa, K. Tetrahedron 1993, 49, 1793.

    51. [51]

      Tao, X. M.; Li, W. F.; Ma, X.; Li, X. M.; Zhu, L. F.; Xie, X. M. Zhang, Z. G. J. Org. Chem. 2012, 77, 8401. 

    52. [52]

      Burk, M. J.; Feaster, J. E.; Nugent, W. A.; Harlow, R. L. J. Am. Chem. Soc. 1993, 115, 10125. 

    53. [53]

      Pye, P. J.; Rossen, K.; Reamer, R. A.; Tsou, N. N.; Volante, R. P.; Reider, P. J. J. Am. Chem. Soc. 1997, 119, 6207. 

    54. [54]

      Burk, M. J. J. Am. Chem. Soc. 1991, 113, 8518. 

    55. [55]

      Burk, M. J.; Feaster, J. E.; Harlow, R. L. Organometallics 1990, 9, 2653. 

    56. [56]

      Burk, M. J. J. Am. Chem. Soc. 1991, 113, 8518. 

    57. [57]

      Burk, M. J.; Feaster, J. E.; Nugent, W. A. J. Am. Chem. Soc. 1993, 115, 10125. 

    58. [58]

      Burk, M. J.; Lee, J. R.; Martinez, J. P. J. Am. Chem. Soc. 1994, 116, 10847. 

    59. [59]

      Achiwa, K. J. Am. Chem. Soc. 1976, 98, 8265. (b) Stille, J. K. Chem. Ind. 1985, 22, 23. 

    60. [60]

      Baker, G. L.; Fritschel, S. J.; Stille, J. R.; Stille, J. K. J. Org. Chem. 1981, 46, 2954. 

    61. [61]

      Takahashi, H.; Hattori, M.; Chiba, M.; Chiwa, A.; Morimoto, T. Tetrahedron Lett. 1986, 27, 4477.

    62. [62]

      RajanBabu, T. V.; Ayers, T. A.; Halliday, G. A.; You, K. K.; Calabrese, J. C. J. Org. Chem. 1997, 62, 6012. 

    63. [63]

      Habus, I.; Raza, Z.; Sunjic, V. J. Mol. Catal. 1987, 42, 173. 

    64. [64]

      Fryzuk, M. D.; Bosnich, B. J. Am. Chem. Soc. 1977, 99, 6262. 

    65. [65]

      Behar, D.; Neta, P. J. Am. Chem. Soc. 1981, 103, 2280. 

    66. [66]

      Miyashita, A.; Yasuda, A.; Takaya, H.; Toriumi, K.; Ito, T.; Noyori, R. J. Am. Chem. Soc. 1980, 102, 7932. 

    67. [67]

      Miyashita, A.; Takaya, H.; Souchi, T.; Noyori, R. Tetrahedron 1984, 40, 1245.

    68. [68]

      Takaya, H.; Mashima, K.; Koyano, K.; Yagi, M.; Kumobayashi, H.; Taketomi, T.; Akutagawa, S.; Noyori, R. J. Org. Chem. 1986, 51, 629. 

    69. [69]

      Takaya, H.; Akutagawa, S.; Noyori, R. Org. Synth. 1988, 67, 20.

    70. [70]

      Burk, M. J. J. Am. Chem. Soc. 1991, 113, 8518. 

    71. [71]

      Jiang, Q.; Jiang, Y.; Xiao, D. M.; Zhang, X. Angew. Chem., Int. Ed. Engl. 1998, 37, 1100. 

    72. [72]

      Kyba, E. P.; Sandoval, C. A.; Yamaguchi, Y.; Zhang, X.; Wang, Z.; Kato, K.; Liu, S. T.; Harris, R. L. Organometallics 1983, 2, 1877. 

    73. [73]

      Liu, Y.; Ding, K. L. J. Am. Chem. Soc. 2005, 127, 10488. (b) Yan Liu, Christian, A.; Ding, K. L. J. Am. Chem. Soc. 2006, 128, 14212 

    74. [74]

      Schmid, R.; Broger, E. A.; Cereghetti, M.; Crameri,Y.; Foricher, J Pure Appl. Chem. 1996, 68, 131.

    75. [75]

      Philip, J. P.; Rossen, K.; Robert, A. R.; Tsou, N. N.; Volante, R. P.; Reider, P. J. J. Am. Chem. Soc. 1997, 119, 6207. 

    76. [76]

      Brenchley, G.; Erifield, E.; Wills, M.; Fedouloff, M. Tetrahedron Lett, 1994, 35, 2791.

    77. [77]

      Sennlenn, P.; Gabler, B.; Helmchen, W. Tetrahedron Lett. 1994, 35, 8595.

    78. [78]

      Whitesell, J. K. Chem. Rev. 1989, 89, 1581. 

    79. [79]

      Kumar, A.; Srivastava, N.; Mital, A. J. Chem. Soc., Chem. Commun. 1992, 32, 493.

    80. [80]

      Jing, Y. Z.; Mi, A.; Yan, M.; Sun, J.; Lou, R. L.; Deng, L. G. J. Am. Chem. Soc. 1997, 119, 9570. 

    81. [81]

      Chan, A.; Jiang, S. C.; Mi, A. Q. US 005756799, 1998[Chem. Abstr. 1998, 129, 54456].

    82. [82]

      Han, Z. B.; Wang, Z.; Zhang, X. M.; Ding. K. L. Angew. Chem., Int. Ed. 2009, 48, 5345 

    83. [83]

      Wang, X. M.; Han, Z. B.; Wang, Z.; Ding, K. L. Angew. Chem., Int. Ed. 2012, 51, 936. (b) Wang, X. B.; Guo, P. H.; Wang, X. M.; Wang, Z.; Ding, K. L. Adv. Synth. Catal. 2013, 355, 2900 

    84. [84]

      Wang, X. M.; Meng, F. Y.; Wang, Y.; Han, Z. B.; Chen, Y. J. Angew. Chem., Int. Ed. 2012, 51, 9276. (b) Cao, Z. Y.; Wang, X.; Tan, C.; Zhao, X. L.; Ding, K. L. J. Am. Chem. Soc. 2013, 135, 8197. (c) Wang, X. M.; Guo, P. H.; Han, Z. B.; Wang, X. B.; Wang, Z.; Ding, K. L. J. Am. Chem. Soc. 2014, 136, 405. (d) Liu, J. W.; Han, Z. B.; Wang, X. M.; Ding, K. L. J. Am. Chem. Soc. 2015, 137, 15346 

    85. [85]

      Alain, R.; Francing, A.; Mortreux, A.; Petit, F. Tetrahedron:Asymmetry 1993, 4, 2279.

    86. [86]

      Alain, R.; Isabelle, S.; Marc, D.; Carpentier, L. F.; Agbossou, F.; Mortreux, A. Tetrahedron:Asymmetry 1996, 7, 379. 

    87. [87]

      Said, N.; Isabell, S.; Mortreux, A.; Agbossou, F.; Mustapha, A. A.; Karim, A. Tetrahedron Lett. 2001, 41, 2867.

    88. [88]

      Tamao, K.; Yamamoto, H.; Matsumoto, H.; Miyake, N.; Hayashi, T.; Kumda, M. Tetrahedron Lett. 1977, 18, 1389.

    89. [89]

      Noyori, R.; Ohta, M.; Hsiao, Y.; Kitamura, M.; Ohta, T.; Takaya, H. J. Am. Chem. Soc. 1986, 108, 7117. 

    90. [90]

      Stille, J. K.; Su, H.; Brechot, P.; Parrinello, G. Organometallics 1991, 10, 1123.

    91. [91]

      Rosini, C.; Franzini, L.; Raffaclli, A. Synthesis 1992, 503.

    92. [92]

      Zhang, F. Y.; Pai, C. C.; Chan, A. S. J. Am. Chem. Soc. 1998, 120, 5808. 

    93. [93]

      Hu, X. Q.; Chen, H. L.; Zhang, X. M. Angew. Chem., Int. Ed. 1999, 38, 3518. 

    94. [94]

      Ogasawara, M.; Yoshida, K.; Kamei, H.; Kato, K.; Uozumi, Y.; Hayshi, T. Tetrahedron:Asymmetry 1998, 9, 1779.

    95. [95]

      Imai, Y.; Zhang, W. B.; Kida, T.; Nakatsuji, Y.; Ikeda, I. Tetrahedron Lett. 1998, 39, 4343.

    96. [96]

      Zhang, Z. G.; Qian, H.; Zhang, X. M. J. Org. Chem. 2000, 65, 6223. 

    97. [97]

      Schmid, R.; Gereghetti, M.; Heiser, B. Helv. Chem. Acta 1988, 71, 897. 

    98. [98]

      Liu, F.; Qian, D. Y.; Li, L.; Zhao, X. L.; Zhang, J. L. Angew. Chem., Int. Ed. 2010, 49, 6669. 

    99. [99]

      Zhang, Z. M.; Chen, P.; Li, W. B.; Niu, Y. F.; Zhao, X. L.; Zhang, J. L. Angew. Chem., Int. Ed. 2014, 53, 4350. 

    100. [100]

      Duclos, M. C.; Singjunla, Y.; Petit, C.; Favre, R. A.; Jeanneau, E.; Popowycz, F.; Lemaire, M. Tetrahedron Lett. 2012, 53, 5984.

    101. [101]

      Yan, Y. J.; Zhang, X. M. J. Am. Chem. Soc. 2006, 128, 7198. 

    102. [102]

      Desponds, O.; Schlosser, M. J. Organomet. Chem. 1996, 507, 257. 

    103. [103]

      Jendralla, H.; Li, C. H.; Paulaus, E. Tetrahedron:Asymmetry 1994, 5, 1297. 

    104. [104]

      Schimid, R.; Broger, E. A.; Cereghetti, M. Pure Appl. Chem. 1996, 68, 131.

    105. [105]

      Murata, M.; Morimoto, T.; Achiwa, K. Synlett 1991, 827.

    106. [106]

      Svensson, G.; Albertsson, J.; Frejd, T. Acta Crystallogr. 1986, 5324.

    107. [107]

      Schimid, R.; Foricher, J.; Cereghetti, M.; Schonholzer, P. Helv. Chim. Acta 1991, 74, 370. 

    108. [108]

      Yamamoto, W.; Murata, M.; Morimoto, S.; Achiwa, K. Chem. Pharm. Bull. 1991, 39, 1085. 

    109. [109]

      Schmid, R.; Ceregheti, M.; Heiser, B.; Schonholzer, P.; Hansan, H. J. Helv. Chim. Acta 1988, 71, 897. 

    110. [110]

      Sun, X. F.; Zhou, L.; Li, W.; Zhang, X. M. J. Org. Chem. 2008, 73, 1143. 

    111. [111]

      Liu, T. L.; Li, W.; Wang, C. J.; Zhang, X. M. Org. Lett. 2013, 15, 1740. 

    112. [112]

      Wang, C. J.; Gao, F.; Liang, G. Org. Lett. 2008, 10, 4711. (b) Wang, C. J.; Liang, G.; Xue, Z. Y.; Gao, F. J. Am. Chem. Soc. 2008, 130, 17250.

    113. [113]

      Xue, Z. Y.; Liu, T. L.; Lu, Z.; Wang, C. J. Chem. Commun. 2010, 46, 1727. 

    114. [114]

      Li, Q. H.; Tong, M. C.; Li, J.; Wang, C. J. Chem. Commun. 2011, 47, 11110. 

    115. [115]

      Li, Q. H.; Liu, T. L.; Zhou, X.; Wang, C. J. Chem. Commun. 2013, 49, 9642. 

    116. [116]

      Liu, H. C.; Tao, H. Y.; Cong, H. J.; Wang. C. J. J. Org. Chem.2016, 81, 3751.

    117. [117]

      Benincori, T.; Brenna, E.; Sannicolo, F. J. Org. Chem. 1997, 62, 444. 

    118. [118]

      Benincori, T.; Brenna, E.; Sannicolo, F.; Trimarco, L.; Antognazza, P.; Cesarotti, E.; Demartin F.; Pilati, T. J. Org. Chem. 1996, 61, 6244. 

    119. [119]

      Gelpke, A. E. S.; Kooijman, H.; Spek, A. L.; Hiemstra, H. Chem. Eur. J. 1999, 5, 2472. 

    120. [120]

      Tietze, L. F.; Thede, K.; Sannicolo, F. Chem. Commun. 1999, 1811.

    121. [121]

      Berens, U.; Brown, J. M.; Long, J.; Selke, R. Tetrahedron:Asymmetry 1996, 7, 285. 

    122. [122]

      McCarthy, M.; Guiry, P. J. Tetrahedron 1999, 55, 3061. 

    123. [123]

      Marquarding, D.; Klusaak, H.; Gokel, G.; Hoffmann, P.; Ugi, I. J. Am. Chem. Soc. 1970, 92, 5389. 

    124. [124]

      Richards, C. J.; Locke, A. J. Tetrahedron:Asymmetry 1998, 9, 2377. 

    125. [125]

      You, S. L.; Hou, X. L.; Dai, L. X.; Yu, Y. H.; Xia, W. J. Org. Chem. 2002, 67, 4684. 

    126. [126]

      Mathey, F.; Mercier, F.; Robin, F.; Ricard, L. J. Organoment. Chem. 1998, 557, 117. 

    127. [127]

      Hayashi, T.; Yamamoto, A.; Hojo, M. J. Am. Chem. Soc. 1982, 104, 180. 

    128. [128]

      Ogasawara, M.; Yoshida, K.; Hayashi, T. Organometallics 2001, 20, 1014. (b) Ogasawara, M.; Yoshida, K.; Hayashi, T. Organometallics 2001, 20, 3913.

    129. [129]

      Wang, M. C.; Xu, C. L.; Zou, Y. X.; Liu, H. M.; Wang, D. K. Tetrahedron Lett. 2005, 46, 5413. (b) Wang, M. C.; Liu, L. T.; Hua, Y. Z.; Zhang, J. S.; Shi, Y. Y.; Wang, D. K. Tetrahedron:Asymmetry 2005, 16, 2531. 

    130. [130]

    131. [131]

    132. [132]

      Pfaltz, A. Acta Chem. Scand B 1996, 50, 189. 

    133. [133]

      Reetz, M. T.; Gosberg, A.; Goddard, R.; Kyung, S. H. Chem. Commun. 1998, 2077.

    134. [134]

      Chi, Y. X.; Zhou, Y. G.; Zhang, X. M. J. Org. Chem. 2003, 68, 4120. (b) Hou, G. H.; Li, W.; Ma, M. F.; Zhang, X. M. J. Am. Chem. Soc. 2010, 132, 12844. 

    135. [135]

      Zhao, Q. Y.; Li, S. K.; Huang, K. X.; Zhang, X. M. Org. Lett. 2013, 15, 4014. 

    136. [136]

      Li, P.; Zhou, M.; Zhao, Q. Y.; Wu, W. L.; Zhang, X. M. Org. Lett. 2016, 18, 40. 

    137. [137]

      Reetz, M. T.; Gosberg, A.; Goddard, R.; Kyung, S. H. Chem. Commun. 1998, 2077.

    138. [138]

      Kless, A.; Lefber, C.; Spannenberg, A.; Kempe, R.; Baumann, W.; Hola, J.; Armin, B. Tetrahedron 1996, 52, 14599.

    139. [139]

      Mayer, H. A.; Otto, H.; Kuhbauch, H. J. Organomet. Chem. 1994, 472, 347. 

    140. [140]

      Delapierre, G.; Brurel, J. M.; Constantieux, T.; Buono, G. Tetrahedron:Asymmetry 2001, 12, 1345. 

    141. [141]

      Reeta, M. T.; Beuttenmuller, E. W.; Goddard, R. Tetrahedron Lett. 1997, 38, 3211. 

    142. [142]

      Zhu, G. X.; Cao, P.; Jiang, Q. Z.; Zhang, X. M. J. Am. Chem. Soc. 1997, 119, 1799. 

    143. [143]

      Alexakis, A.; Burton, J.; Vastra, J.; Mangeney, P. Tetrahedron:Asymmetry 1997, 8, 3987.

    144. [144]

      Brunel, J. M.; Constantieux, T.; Legrand, O.; Buono, G. Tetrahedron Lett. 1998, 39, 2961.

    145. [145]

      Sugihara, H.; Daikai, K.; Jin, X. L.; Furuno, H.; Inanaga, J. Tetrahedron Lett. 2002, 43, 2735. 

    146. [146]

    147. [147]

    148. [148]

      Hayashi, T.; Kawamara, N.; Ito, Y. J. Am. Chem. Soc. 1987, 109, 7876. 

    149. [149]

      Sayo, N.; Taketomi, T.; Kumobayashi, H. EP 271311, 1988[Chem. Abstr. 1989, 110, 39189].

    150. [150]

    151. [151]

      Parrinello, G.; Stille, J. K. J. Am. Chem. Soc. 1987, 109, 7122. 

    152. [152]

      Ishizaki, T. EP 5444551993[Chem. Abstr. 1993, 119, 181016.]

    153. [153]

      Dumont, W.; Poalin, J. C.; Dang, T. P.; Kagan, H. B. J. Am. Chem. Soc. 1973, 95, 8295. 

    154. [154]

      Takaishi, N.; Jmai, H.; Bertelo, C. A.; Stille, J. K. J. Am. Chem. Soc. 1978, 100, 264. 

    155. [155]

      Poulin, J. C.; Dumont, W.; Dang, T. P.; Kagan, H. B. Compt. Rend. Acad. Sci. Paris 1973, 227C, 41.

    156. [156]

      Stille, J. K. React. Polym. 1989, 10, 165. 

    157. [157]

    158. [158]

      Wan, K. T.; Davis, M. E. Nature 1994, 370, 449. 

    159. [159]

      Cheng, Z. B.; Yu, S. L.; Li, Y. Y. Chem. Res. Chin. Univ. 2011, 27, 170.

    160. [160]

      Yu, S. L.; Li, Y. Y.; Dong, Z. R.; Zhang, J. N.; Li, Q.; Gao, J. X. Chin. Chem. Lett. 2011, 22, 1269. 

    161. [161]

      Zhang, J. N.; Yang, X. R.; Zhou, H.; Li, Y. Y.; Dong, Z. R.; Gao, J. X. Green Chem. 2012, 14, 1289. 

    162. [162]

      Xu, Y. Q.; Yu, S. L.; Li, Y. Y.; Dong, Z. R.; Gao, J. X. Chin. Chem. Lett. 2013, 24, 527. 

    163. [163]

      Zeng, L.; Wu, F.; Li, Y. Y. J. Org. Chem. 2014, 762, 34. 

    164. [164]

      Trost, B. M.; Brendan, M. Org. Lett. 2008, 10, 1369.

    165. [165]

       

    166. [166]

      Hu, A. G.; Fu, Y.; Xie, J. H.; Zhou, Q. L. Angew. Chem., Int. Ed. 2002, 41, 2348. (b) Fu, Y.; Xie, J. H.; Hu, A. G.; Zhou, H.; Wang, L. X.; Zhou, Q. L. Chem. Commun. 2002, 480. 

    167. [167]

      Xie, J. H.; Wang, L. X.; Fu, Y.; Zhu, S. F.; Fan, B. M.; Duan, H. F.; Zhou, Q. L. J. Am. Chem. Soc. 2003, 125, 4404. (b) Zhu, G. X.; Cao, P.; Jiang, Q. Z.; Zhang, X. M. J. Am. Chem. Soc. 1997, 119, 1799. 

    168. [168]

      Han, Z. B.; Wang, Z.; Zhang, X. M.; Ding, K. Angew. Chem., Int. Ed. 2009, 48, 5345. 

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