Citation: Zhou Qiwen, Feng Xiangqing, Yang Jing, Du Haifeng. Asymmetric Transfer Hydrogenations of β-Enamine Cyanide with Chiral Ammonia Borane[J]. Chinese Journal of Organic Chemistry, ;2019, 39(8): 2188-2195. doi: 10.6023/cjoc201904079 shu

Asymmetric Transfer Hydrogenations of β-Enamine Cyanide with Chiral Ammonia Borane

a.
Key Laboratory of Chemical Resource Engineering Beijing Key Laboratory of Bioprocess, College of Life Sciences and Technology, Beijing University of Chemical Technology, Beijing 100029
b.
Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190

Corresponding author: Yang Jing, yangji@mail.buct.edu.cn Du Haifeng, haifengdu@iccas.ac.cn
Received Date: 30 April 2019
Revised Date: 6 June 2019
Available Online: 12 August 2019
Fund Project: the National Natural Science Foundation of China 21825108the National Natural Science Foundation of China 91856103Project supported by the National Natural Science Foundation of China (Nos. 21825108, 91856103)

Figures(2)

The asymmetric transfer hydrogenation represents one important class of reactions for the synthesis of optically active compounds. A chiral ammonia borane was generated in situ from an H₂ release reaction between chiral phosphoric acid and ammonia borane, which could be regenerated by the assistance of water after the hydrogen transfer process and made this reaction catalytic. With this chiral ammonia borane, asymmetric transfer hydrogenations of β-enamine cyanides were realized to afford the desired products in 48%~98% yields with 61%~95% ee.
- asymmetric transfer hydrogenation,
- chiral ammonia borane,
- chiral phosphoric acid,
- ammonia borane,
- β-enamino cyanide
1. [1]
  For selected reviews, see: (a) Noyori, R.; Hashiguchi, S. Acc. Chem. Res. 1997, 30, 97.
  (b) Gladiali, S.; Alberico, E. Chem. Soc. Rev. 2006, 35, 226.
  (c) Ikariya, T.; Blacker, A. J. Acc. Chem. Res. 2007, 40, 1300.
  (d) Zhang, Z.; Butt, N. A.; Zhou, M.; Liu, D.; Zhang, W. Chin. J. Chem. 2018, 36, 443.
  (e) Zhang, Z.; Butt, N. A.; Zhang, W. Chem. Rev. 2016, 116, 14769.
2. [2]
  Hantzsch, A. Justus Liebigs Ann. Chem. 1882, 215, 1. doi: 10.1002/jlac.18822150102
3. [3]
  Mumm, O.; Diederichsen, J. Justus Liebigs Ann. Chem. 1839, 538, 195.
4. [4]
  Berg, J. M.; Tymoczko, J. L.; Stryer, L. Biochemistry, 5th ed., W. H. Freeman and Company, New York, 2002.
5. [5]
  (a) Ouellet, S. G.; Walji, A. M.; MacMillan, D. W. C. Acc. Chem. Res. 2007, 40, 1327.
  (b) Zheng, C.; You, S.-L. Chem. Soc. Rev. 2012, 41, 2498.
  (c) McSkimming, A.; Colbran, S. B. Chem. Soc. Rev. 2013, 42, 5439.
  (d) Phillips, A. M. F.; Pombeiro, A. J. L. Org. Biomol. Chem. 2017, 15, 2307.
6. [6]
  (a) Shore, S. G.; Parry, R. W. J. Am. Chem. Soc. 1955, 77, 6084.
  (b) Stephens, F. H.; Pons, V.; Baker, R. T. Dalton Trans. 2007, 2613.
  (c) Staubitz, A.; Robertson, A. P. M.; Manners, I. Chem. Rev. 2010, 110, 4079.
7. [7]
  (a) Hamilton, C. W.; Baker, R. T.; Staubitz, A.; Manners, I. Chem. Soc. Rev. 2009, 38, 279.
  (b) Marder, T. B. Angew. Chem., Int. Ed. 2007, 46, 8116.
  (c) Gutowska, A.; Li, L.; Shin, Y.; Wang, C. M.; Li, X. S.; Linehan, J. C.; Smith, R. S.; Kay, B. D.; Schmid, B.; Shaw, W.; Gutowski, M.; Autrey, T. Angew. Chem., Int. Ed. 2005, 44, 3578.
  (d) Grochala, W.; Edwards, P. P. Chem. Rev. 2004, 104, 1283.
8. [8]
  Yang, X.; Zhao, L.; Fox, T.; Wang, Z.-X.; Berke, H. Angew. Chem., Int. Ed. 2010, 49, 2058. doi: 10.1002/anie.200906302
9. [9]
  Yang, X.; Fox, T.; Berke, H. Chem. Commun. 2011, 47, 2053. doi: 10.1039/c0cc03163a
10. [10]
  Yang, X.; Fox, T.; Berke, H. Org. Biomol. Chem. 2012, 10, 852. doi: 10.1039/C1OB06381B
11. [11]
  Yang, X.; Fox, T.; Berke, H. Tetrahedron 2011, 67, 7121. doi: 10.1016/j.tet.2011.06.104
12. [12]
  Xu, W.; Fan, H.; Wu, G.; Chen, P. New J. Chem. 2012, 36, 1496. doi: 10.1039/c2nj40227k
13. [13]
  Winner, L.; Ewing, W. C.; Geetharani, K.; Dellermann, T.; Jouppi, B.; Kupfer, T.; Braunschweig, H. Angew. Chem., Int. Ed. 2018, 57, 12275. doi: 10.1002/anie.201807435
14. [14]
  For selected examples, for the metal organic catalysts see: (a) Chong, C. C.; Hirao, H.; Kinjo, R. Angew. Chem., Int. Ed. 2014, 53, 3342.
  (b) Ding, F.; Zhang, Y.; Jiang, Y.; Bao, R. L.; Lin, K.; Shi, L. Chem. Commun. 2017, 53, 9262.
  (c) Zhou, Q.; Zhang, L.; Yang, J.; Du, H. Org. Lett. 2016, 18, 5189.
15. [15]
  For selected examples, for the metal catalysts see: (a) Fu, S.; Chen, N.-Y.; Liu, X.; Shao, Z.; Luo, S.-P.; Liu, Q. J. Am. Chem. Soc. 2016, 138, 8588.
  (b) Shao, Z.; Fu, S.; Wei, M.; Zhou, S.; Liu, Q. Angew. Chem., Int. Ed. 2016, 55, 1463.
  (c) Das, M.; Kaicharla, T.; Teichert, J. F. Org. Lett. 2018, 20, 4926.
  (d) Ménard, G.; Stephan, D. W. J. Am. Chem. Soc. 2010, 132, 1796.
16. [16]
  For selected examples, for the nanoparticles see:
  (a) Vasilikogiannaki, E.; Gryparis, C.; Kotzabasaki, V.; Lykakis, I. N.; Stratakis, M. Adv. Synth. Catal. 2013, 355, 907.
  (b) Metin, Ö.; Mendoza-Garcia, A.; Dalmızrak, D.; Gültekin, M. S.; Sun, S. Catal. Sci. Technol. 2016, 6, 6137.
  (c) Lara, P.; Philippot, K.; Suárez, A. ChemCatChem 2019, 11, 766.
17. [17]
  Allwood, B. L.; Shahriari-Zavareh, H.; Stoddart, J. F.; Williams, D. J. J. Chem. Soc., Chem. Commun. 1984, 1461.
18. [18]
  Li, S.; Li, G.; Meng, W.; Du, H. J. Am. Chem. Soc. 2016, 138, 12956. doi: 10.1021/jacs.6b07245
19. [19]
  Li, S.; Meng, W.; Du, H. Org. Lett. 2017, 19, 2604. doi: 10.1021/acs.orglett.7b00935
20. [20]
  Zhao, W.; Feng, X.; Yang, J.; Du, H. Tetrahedron Lett. 2019, 60, 1193. doi: 10.1016/j.tetlet.2019.03.060
21. [21]
  Zhou, Q.; Meng, W.; Yang, J.; Du, H. Angew. Chem., Int. Ed. 2018, 57, 12111. doi: 10.1002/anie.201806877
22. [22]
  Xie, J. H.; Zhu, S. F.; Zhou, Q. L. Chem. Rev. 2011, 111, 1713. doi: 10.1021/cr100218m
23. [23]
  Xie, J. H.; Zhu, S. F.; Zhou, Q. L. Chem. Soc. Rev. 2012, 41, 4126. doi: 10.1039/c2cs35007f
24. [24]
  Ye, J.; Wang, C.; Chen, L.; Wu, X.; Zhou, L.; Sun, J. Adv. Synth. Catal. 2016, 358, 1042. doi: 10.1002/adsc.201501061
25. [25]
  Malkov, A. V.; Stončius, S.; Vrankova, K.; Arndt, M.; Kočovský P. Chem.-Eur. J. 2008, 14, 8082. doi: 10.1002/chem.200801244
26. [26]
  Yu, W.; Du, Y.; Zhao, K. Org. Lett. 2009, 11, 2417. doi: 10.1021/ol900576a
27. [27]
  Sun, P.; Zhang, Y. Synth. Commun. 1997, 27, 3175. doi: 10.1080/00397919708004176
28. [28]
  Leon, M. A.; Liu, X.; Phan, J. H.; Clift, M. D. Eur. J. Org. Chem. 2016, 4508.
29. [29]
  Wu, M.; Jiang, Y.; An, Z.; Qi, Z.; Yan, R. Adv. Synth. Catal. 2018, 360, 4236. doi: 10.1002/adsc.201800693
30. [30]
  Aniguchi, T.; Goto, N.; Ishibashi, H. Tetrahedron Lett. 2009, 50, 4857. doi: 10.1016/j.tetlet.2009.06.014
31. [31]
  Poisson, T.; Gembus, V.; Oudeyer, S.; Marsais, F.; Levacher, V. J. Org. Chem. 2009, 74, 3516. doi: 10.1021/jo802763b
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