Citation: Li Zhen, Duan Weiliang. Recent Advances in the Asymmetric Conjugate Addition Reactions of Phosphorus Nucleophiles to Electron-Deficient Alkenes[J]. Chinese Journal of Organic Chemistry, ;2016, 36(8): 1805-1813. doi: 10.6023/cjoc201602018 shu

Recent Advances in the Asymmetric Conjugate Addition Reactions of Phosphorus Nucleophiles to Electron-Deficient Alkenes

Li Zhen ^a ,
Duan Weiliang ^b,*,,

a.
School of Chemical and Environmental Engineering, Shanghai Institute of Technology, Shanghai 201418
b.
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032

Corresponding author: Duan Weiliang, wlduan@mail.sioc.ac.cn
Received Date: 19 February 2016
Revised Date: 20 April 2016

Fund Project: Project supported by the National Natural Science Foundation of China Nos. 20902099，21172238，21472218

Figures(15)

Chiral phosphines are very useful in the fields of asymmetric catalysis, pharmaceutical chemistry, and materials. These compounds have been used as ligands coordinated to transition metals or organocatalysts in various reactions to furnish optically active products with high efficiency. Asymmetric phosphorus-addition reaction can be utilized for the direct preparation of chiral phosphorus compounds. This review summarizes the recent progress in the field of enantioselective phosphorus-addition reactions. Several examples of transition metal- and organocatalyst-promoted asymmetric hydrophosphination reactions of electron-deficient alkenes have been introduced.
- asymmetric addition,
- phosphorus nucleophiles,
- chiral phosphorus compounds,
- electron-deficient alkenes
1. [1]
2. [2]
  Kovacik, I.; Wicht, D. K.; Grewal, N. S.; Glueck, D. S.; Incarvito, C. D.; Guzei, I. A.; Rheingold, A. L. Organometallics 2000, 19, 950.(b) Scriban, C.; Kovacik, I.; Glueck, D. S. Organometallics 2005, 24, 4871.
3. [3]
4. [4]
5. [5]
  Sadow, A. D.; Haller, I.; Fadini, L.; Togni, A. J. Am. Chem. Soc. 2004, 126, 14704.(b) Sadow, A. D.; Togni, A. J. Am. Chem. Soc. 2005, 127, 17012.
6. [6]
  Bartoli, G.; Bosco, M.; Carlone, A.; Locatelli, M.; Mazzanti, A.; Sambri, L.; Melchiorre, P. Chem. Commun. 2007, 722.
7. [7]
  Carlone, A.; Bartoli, G.; Bosco, M.; Sambri, L.; Melchiorre, P. Angew. Chem., Int. Ed. 2007, 46, 4504.(b) Ibrahem, I.; Rios, R.; Vesely, J.; Hammar, P.; Eriksson, L.; Himo, F.; Cordova, A. Angew. Chem., Int. Ed. 2007, 46, 4507.(c) Ibrahem, I.; Hammar, P.; Vesely, J.; Rios, R.; Eriksson, L.; Cordova, A. Adv. Synth. Catal. 2008, 350, 1875.
8. [8]
  Feng, J.-J.; Chen, X.-F.; Shi, M.; Duan, W.-L. J. Am. Chem. Soc. 2010, 132, 5562.
9. [9]
10. [10]
  Du, D.; Duan, W.-L. Chem. Commun. 2011, 47, 11101.(b) Chen, Y.-R.; Duan, W.-L. Org. Lett. 2011, 13, 5824.(c) Feng, J.-J.; Huang, M.; Lin, Z.-Q.; Duan, W.-L. Adv. Synth. Catal. 2012, 354, 3122.(d) Du, D.; Lin, Z.-Q.; Lu, J.-Z.; Li, C.; Duan, W.-L. Asian J. Org. Chem. 2013, 2, 392.(e) Lu, J.; Ye, J.; Duan, W.-L. Org. Lett. 2013, 15, 5016.(f) Huang, M.; Li, C.; Duan, W.-L.; Xu, S. Chem. Commun. 2012, 48, 11148.
11. [11]
  Huang, Y.; Pullarkat, S. A.; Li, L.; Leung, P.-H. Chem. Commun. 2010, 6950.
12. [12]
  Huang, Y.; Chew, R. J.; Li, Y.; Pullarkat, S. A.; Leung, P.-H. Org. Lett. 2011, 13. 5862.(b) Huang, Y.; Pullarkat, S. A.; Teong, S.; Chew, R. J.; Li, Y.; Leung, P.-H. Organometallics 2012, 31, 4871.(c) Chew, R. J.; Huang, Y.; Li, Y.; Pullarkat, S. A.; Leung, P.-H. Adv. Synth. Catal. 2013, 355, 1403.(d) Chew, R. J.; Teo, K. Y.; Huang, Y.; Li, B.-B.; Li, Y.; Pullarkat, S. A.; Leung, P.-H. Chem. Commun. 2014, 50, 8768.(e) Chew, R. J.; Lu, Y.; Jia, Y.-X.; Li, B.-B.; Wong, E. H. Y.; Goh, R.; Li, Y.; Huang, Y.; Pullarkat, S. A.; Leung, P.-H. Chem.-Eur. J. 2014, 20, 14514.(f) Chew, R. J.; Sepp, K.; Li, B.-B.; Li, Y.; Zhu, P.-C.; Tan, N. S.; Leung, P.-H. Adv. Synth. Catal. 2015, 357, 3297.
13. [13]
  Yang, X.-Y.; Tay, W. S.; Li, Y.; Pullarkat, S. A.; Leung, P.-H. Organometallics 2015, 34, 5196.(b) Yang, X.-Y.; Tay, W.; Li, Y.; Pullarkat, S.; Leung, P.-H. Chem. Commun. 2016, 52, 4211.
14. [14]
  Yang, M.-J.; Liu, Y.-J.; Gong, J.-F.; Song, M.-P. Organometallics 2011, 30, 3793.(b) Hao, X.-Q.; Zhao, Y.-W.; Yang, J.-J.; Niu, J.-L.; Gong, J.-F.; Song, M.-P. Organometallics 2014, 33, 1801.(c) Hao, X. Q.; Huang, J. J.; Wang, T.; Lv, J.; Gong, J. F.; Song, M. P. J. Org. Chem. 2014, 79, 9512.
15. [15]
  Ding, B.; Zhang, Z.; Xu, Y.; Liu, Y.; Sugiya, M.; Imamoto, T.; Zhang, W. Org. Lett. 2013, 15, 5476.(b) Xu, Y.; Yang, Z.; Ding, B.; Liu, D.; Liu, Y.; Sugiya, M.; Imamoto, T.; Zhang, W. Tetrahedron 2015, 71, 6832.
16. [16]
  For reviews on asymmetric 1,6-addition reactions, see:(a) Csákÿ, A. G.; la Herran, G. de.; Murcia, M. C. Chem. Soc. Rev. 2010, 39, 4080.(b) Biju, A. T. ChemCatChem 2011, 3, 1847.(c) Silva, E. M. P.; Silva, A. M. S. Synthesis 2012, 44, 3109.
17. [17]
  Lu, J.; Ye, J.; Duan, W.-L. Chem. Commun. 2014, 50, 698.(b) Huang, J.; Zhao, M.-X.; Duan, W.-L. Tetrahedron Lett. 2014, 55, 629.
18. [18]
  Huang, Y.; Pullarkat, S. A.; Li, Y.; Leung, P.-H. Inorg. Chem. 2012, 51, 2533.
19. [19]
  Li, C.; Li, W.-X.; Xu, S.; Duan, W.-L. Org. Chem. Front. 2014, 1, 541.
20. [20]
  Chen, Y.-R.; Feng, J.-J.; Duan, W.-L. Tetrahedron Lett. 2014, 55, 595.
21. [21]
  Fu, X.; Jiang, Z.; Tan, C.-H. Chem. Commun. 2007, 5058.
22. [22]
  Zhao, D.; Yuan, Y.; Chan, Albert S. C.; Wang, R. Chem.-Eur. J. 2009, 15, 2738.(b) Zhao, D.; Wang, Y.; Mao, L.; Wang. R. Chem.-Eur. J. 2009, 15, 10983.(c) Zhao, D.; Mao, L.; Wang, Y.; Yang, D.; Zhang, Q.; Wang, R. Org. Lett. 2010, 12, 1880.(d) Zhao, D.; Mao, L.; Yang, D.; Wang, R. J. Org. Chem. 2010, 75, 6756.(e) Zhao, D.; Mao, L.; Wang, L.; Yang, D.; Wang. R. Chem. Commun. 2012, 48, 889.(f) Zhao, D.; Wang, L.; Yang, D.; Zhang, Y.; Wang. R. Chem.-Eur. J. 2012, 7, 881.
23. [23]
  Wen, S.; Li, L.; Wu, H.; Yu, F.; Liang, X.; Ye, J. Chem. Commun. 2010, 4806.
24. [24]
  Russo, A.; Lattanzi, A. Eur. J. Org. Chem. 2010, 6736.
25. [25]
  Luo, X.; Zhou, Z.; Li, X.; Liang, X.; Ye, J. RSC Adv. 2011, 1, 698.
26. [26]
  Hatano, M.; Horibe, T.; Ishihara, K. Angew. Chem., Int. Ed. 2013, 52, 4549.
27. [27]
  Geng, Z-C.; Zhang, J.-X.; Li, N.; Chen, J.; Huang, X.-F.; Zhang, S.-Y.; Li, H.-Y.; Tao, J.-C.; Wang, X.-W. Tetrahedron 2014, 70, 417.
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