SIOC 中文
CJOG
Adv search

Chinese Journal of Organic Chemistry >

2019 , Vol. 39 >Issue 8: 2188 - 2195

DOI: https://doi.org/10.6023/cjoc201904079

Articles

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

  • Zhou Qiwen ,
  • Feng Xiangqing ,
  • Yang Jing ,
  • Du Haifeng
Expand
  • 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

Received date: 2019-04-30

  Revised date: 2019-06-06

  Online published: 2019-06-12

Supported by

Project supported by the National Natural Science Foundation of China (Nos. 21825108, 91856103).

Fold

Abstract

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.

Key words： asymmetric transfer hydrogenation; chiral ammonia borane; chiral phosphoric acid; ammonia borane; β-enamino cyanide

Cite this article

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

References

[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] Hantzsch, A. Justus Liebigs Ann. Chem. 1882, 215, 1.
[3] Mumm, O.; Diederichsen, J. Justus Liebigs Ann. Chem. 1839, 538, 195.
[4] Berg, J. M.; Tymoczko, J. L.; Stryer, L. Biochemistry, 5th ed., W. H. Freeman and Company, New York, 2002.
[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] (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] (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] Yang, X.; Zhao, L.; Fox, T.; Wang, Z.-X.; Berke, H. Angew. Chem., Int. Ed. 2010, 49, 2058.
[9] Yang, X.; Fox, T.; Berke, H. Chem. Commun. 2011, 47, 2053.
[10] Yang, X.; Fox, T.; Berke, H. Org. Biomol. Chem. 2012, 10, 852.
[11] Yang, X.; Fox, T.; Berke, H. Tetrahedron 2011, 67, 7121.
[12] Xu, W.; Fan, H.; Wu, G.; Chen, P. New J. Chem. 2012, 36, 1496.
[13] Winner, L.; Ewing, W. C.; Geetharani, K.; Dellermann, T.; Jouppi, B.; Kupfer, T.; Braunschweig, H. Angew. Chem., Int. Ed. 2018, 57, 12275.
[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] 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] 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.; Dalmizrak, D.; Gültekin, M. S.; Sun, S. Catal. Sci. Technol. 2016, 6, 6137.
(c) Lara, P.; Philippot, K.; Suárez, A. ChemCatChem 2019, 11, 766.
[17] Allwood, B. L.; Shahriari-Zavareh, H.; Stoddart, J. F.; Williams, D. J. J. Chem. Soc., Chem. Commun. 1984, 1461.
[18] Li, S.; Li, G.; Meng, W.; Du, H. J. Am. Chem. Soc. 2016, 138, 12956.
[19] Li, S.; Meng, W.; Du, H. Org. Lett. 2017, 19, 2604.
[20] Zhao, W.; Feng, X.; Yang, J.; Du, H. Tetrahedron Lett. 2019, 60, 1193.
[21] Zhou, Q.; Meng, W.; Yang, J.; Du, H. Angew. Chem., Int. Ed. 2018, 57, 12111.
[22] Xie, J. H.; Zhu, S. F.; Zhou, Q. L. Chem. Rev. 2011, 111, 1713.
[23] Xie, J. H.; Zhu, S. F.; Zhou, Q. L. Chem. Soc. Rev. 2012, 41, 4126.
[24] Ye, J.; Wang, C.; Chen, L.; Wu, X.; Zhou, L.; Sun, J. Adv. Synth. Catal. 2016, 358, 1042.
[25] Malkov, A. V.; Stoncius, S.; Vrankova, K.; Arndt, M.; Kocovský; P. Chem.-Eur. J. 2008, 14, 8082.
[26] Yu, W.; Du, Y.; Zhao, K. Org. Lett. 2009, 11, 2417.
[27] Sun, P.; Zhang, Y. Synth. Commun. 1997, 27, 3175.
[28] Leon, M. A.; Liu, X.; Phan, J. H.; Clift, M. D. Eur. J. Org. Chem. 2016, 4508.
[29] Wu, M.; Jiang, Y.; An, Z.; Qi, Z.; Yan, R. Adv. Synth. Catal. 2018, 360, 4236.
[30] Aniguchi, T.; Goto, N.; Ishibashi, H. Tetrahedron Lett. 2009, 50, 4857.
[31] Poisson, T.; Gembus, V.; Oudeyer, S.; Marsais, F.; Levacher, V. J. Org. Chem. 2009, 74, 3516.

Options
Outlines

/

〈 〉