Catalytic Kinetic Resolution of Amines and Their Derivatives by Non-acylation Reaction

  • Tang Liang ,
  • Li Xuewei ,
  • Xie Fang ,
  • Zhang Wanbin
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  • Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai 200240

Received date: 2019-10-10

  Revised date: 2019-11-11

  Online published: 2020-04-02

Supported by

Project supported by the National Natural Science Foundation of China (No. 21572129).

Abstract

Enantiopure amines are important building blocks with a plethora of applications in the fields of medicine, agriculture and materials. Kinetic resolution (KR) of racemic amines is one of the most important methods for obtaining enantiopure amines. However, KR of amines is little investigated because of their high reactivity and coordinating ability in the corresponding KR of alcohols. Till now, major developments using non-enzymatic catalysts for KR of amines have been extensively achieved by catalytic acylation (or deacylation). Only recently the non-acylation KR of amines is improving. The relatively wide range of different catalytic asymmetric reactions have been employed as strategies for the efficient KR of amines. For some cases, the asymmetric reactions do not involve with nitrogen atoms of racemic substrates. This review aims to introduce the development of the non-acylation KR of amines for the synthesis of enantiopure amines.

Cite this article

Tang Liang , Li Xuewei , Xie Fang , Zhang Wanbin . Catalytic Kinetic Resolution of Amines and Their Derivatives by Non-acylation Reaction[J]. Chinese Journal of Organic Chemistry, 2020 , 40(3) : 575 -588 . DOI: 10.6023/cjoc201910010

References

[1] Yoshimura, H.; Oguri, K.; Tsukamoto, H. Tetrahedron Lett. 1968, 9, 483.
[2] Lautens, M.; Rovis, T. J. Org. Chem. 1997, 62, 5246.
[3] Jeffery, J. E.; Kerrigan, F.; Miller, T. K.; Smith, G. J.; Tometzki, G. B. J. Chem. Soc., Perkin Trans. 1996, 2583.
[4] Stoner, E. J.; Cooper, A. J.; Diclcman, D. A.; Kolaczkowslti, L.; Lallaman, J. E.; Liu, J. H.; Oliver-Shaffer, P A.; Patel, K. M.; Paterson, J. B.; Plata, D. J.; Riley, D. A.; Sham, H. L.; Stengel, P J.; Tien, J. H. Org. Proc. Res. Dev. 2000, 4, 264.
[5] France, S.; Guerin, D. J.; Miller, S. J.; Lectka, T. Chem. Rev. 2003, 103, 2985.
[6] (a) Vedejs, E.; Jure, M. Angew. Chem., Int. Ed. 2005, 44, 3974.
(b) Kagan, H. B.; Fiaud, J.-C. Top. Stereochem. 1988, 18, 249.
[7] Keith, J. M.; Larrow, J. F.; Jacobsen, E. N. Adv. Synth. Catal. 2001, 343, 5.
[8] (a) Arai, S.; Bellemin-Laponnaz, S.; Fu, G. C. Angew. Chem., Int. Ed. 2001, 40, 234.
(b) De, C. K.; Klauber, E. G.; Seidel, D. J. Am. Chem. Soc. 2009, 131, 17060.
(c) Klauber, E. G.; De, C. K.; Shah, T. K.; Seidel, D. J. Am. Chem. Soc. 2010, 132, 13624.
(d) Mittal, N.; Lippert, K. M.; De, C. K.; Klauber, E. G.; Emge, T. J.; Schreiner, P. R.; Seidel, D. J. Am. Chem. Soc. 2015, 137, 5748.
(e) Birman, V. B.; Jiang, H.; Li, X.; Guo, L.; Uffman, E. W. J. Am. Chem. Soc. 2006, 128, 6536.
(f) Yang, X.; Bumbu, V. D.; Liu, P.; Li, X.; Jiang, H.; Uffman, E. W.; Guo, L.; Zhang, W.; Jiang, X.; Houk, K. N.; Birman, V. B. J. Am. Chem. Soc. 2012, 134, 17605.
(g) Arseniyadis, S.; Valleix, A.; Wagner, A.; Mioskowski, C. Angew. Chem., Int. Ed. 2004, 43, 3314.
(h) Arseniyadis, S.; Subhash, P. V.; Valleix, A.; Mathew, S. P.; Blackmond, D. G.; Wagner, A.; Mioskowski, C. J. Am. Chem. Soc. 2005, 127, 6138.
[9] (a) Birman, V. B.; Jiang, H.; Li, X.; Guo, L.; Uffman, E. W. J. Am. Chem. Soc. 2006, 128, 6536.
(b) Yang, X.; Bumbu, V. D.; Liu, P.; Li, X.; Jiang, H.; Uffman, E. W.; Guo, L.; Zhang, W.; Jiang, X.; Houk, K. N.; Birman, V. B. J. Am. Chem. Soc. 2012, 134, 17605.
(c) Fowler, B. S.; Mikochik, P. J.; Miller, S. J. J. Am. Chem. Soc. 2010, 132, 2870.
(d) Bumbu, V. D.; Yang, X.; Birman, V. B. J. Am. Chem. Soc. 2011, 133, 13902.
(e) Bumbu, V. D.; Yang, X.; Birman, V. B. Org. Lett., 2013, 15, 279.
[10] For representative reports on OKR, see: (a) Ferreira, E. M.; Stoltz, B. M. J. Am. Chem. Soc. 2001, 123, 7725.
(b) Muller, J. A.; Sigman, M. S. J. Am. Chem. Soc. 2003, 125, 7005.
(c) Nishibayashi, Y.; Yamauchi, A.; Onodera, G.; Uemura, S. J. Org. Chem. 2003, 68, 5875.
(d) Radosevich, A. T.; Musich, C.; Toste, F. D. J. Am. Chem. Soc. 2005, 127, 1090.
(e) Pawar, V. D.; Bettigeri, S.; Weng, S.-S.; Kao, J.-Q.; Chen, C.-T. J. Am. Chem. Soc. 2006, 128, 6308.
(f) Chen, T.; Jiang, J.-J.; Xu, Q.; Shi, M. Org. Lett. 2007, 9, 865.
(g) Arita, S.; Koike, T.; Kayaki, Y.; Ikariya, T. Angew. Chem., Int. Ed. 2008, 49, 2447.
(h) Tomizawa, M.; Shibuya, M.; Iwabuchi, Y. Org. Lett. 2009, 11, 1829.
(i) Kunisu, T.; Oguma, T.; Katsuki, T. J. Am. Chem. Soc. 2011, 133, 12937.
[11] (a) Miyano, S.; Lu, L. D.-L.; Viti, S. M.; Sharpless, K. B. J. Org. Chem. 1983, 48, 3608.
(b) Miyano, S.; Lu, L. D.-L.; Viti, S. M.; Sharpless, K. B. J. Org. Chem. 1985, 50, 4350.
(c) Hayashi, M.; Okamura, M.; Toba, T.; Oguni, N.; Sharpless, K. B. Chem. Lett. 1990, 547.
[12] Bhadra, S.; Yamamoto, H. Angew. Chem., Int. Ed. 2016, 55, 13043.
[13] Saito, K.; Shibata, Y.; Yamanaka, M.; Akiyama, T. J. Am. Chem. Soc. 2013, 135, 11740.
[14] (a) Tsutsui, H.; Narasaka, K. Chem. Lett. 1999, 28, 45.
(b) Tsutsui, H.; Kitamura, M.; Narasaka, K. Bull. Chem. Soc. Jpn. 2002, 75, 1451.
[15] Saito, K.; Akiyama, T. Angew. Chem., Int. Ed. 2016, 55, 3148.
[16] Lu, R.; Cao, L.; Guan, H.; Liu, L. J. Am. Chem. Soc. 2019, 141, 6318.
[17] (a) Tanner, D. Angew. Chem., Int. Ed. Engl. 1994, 33, 599.
(b) Fruit, C.; Müller, P. Chem. Rev. 2003, 103, 2905.
[18] Cockrell, J.; Wilhelmsen, C.; Rubin, H.; Martin, A.; Morgan, J. B. Angew. Chem., Int. Ed. 2012, 51, 9842.
[19] Ohmatsu, K.; Hamajima, Y.; Ooi, T. J. Am. Chem. Soc. 2012, 134, 8794.
[20] Ohmatsu, K.; Ando, Y.; Ooi, T. J. Am. Chem. Soc. 2013, 135, 18706.
[21] Monaco, M.R.; Poladura, B.; De Los Bernardos, M. D.; Leutzsch, M.; Goddard, R.; List, B. Angew. Chem., Int. Ed. 2014, 53, 7063.
[22] Zhu, Y. M.; Yang, P. J.; Wang, S.; Liu, Z.; Yang, G.; Chai, Z. J. Am. Chem. Soc. 2015, 137, 10088.
[23] Yang, P. J., Zhang, H.; Wang, S.; Yang, G.; Chai, Z. Angew. Chem., Int. Ed. 2017, 56, 650.
[24] Zhang, F.; Zhang, Y.; Tan, Q.; Lin, L.; Liu, X.; Feng, X. Org. Lett. 2019, 21, 5928.
[25] Chen, X.; Vedejs, W. J. Am. Chem. Soc. 1997, 119, 2584.
[26] Wu, B.; Parquette, J. R.; RajanBabu, T. V. Science 2009, 326, 1662.
[27] Wu, B.; Gallucci, J. C.; Parquette, J. R.; RajanBabu, T. V. Chem. Sci. 2014, 5, 1102.
[28] Xu, Y.; Kaneko, K.; Kanai, M.; Shibasaki, M.; Matsunaga, S. J. Am. Chem. Soc. 2014, 136, 9190.
[29] Hu, H.; Liu, Y.; Lin, L.; Zhang, Y.; Liu, X.; Feng, X. Angew. Chem., Int. Ed. 2016, 55, 10098.
[30] An, D.; Guan, X.; Guan, R.; Jin, L.; Zhang, G.; Zhang, S. Chem. Commun. 2016, 52, 11211.
[31] Zheng, B. H.; Hou, X.-L. Org. Lett. 2009, 11, 1789.
[32] Wang, Y., Xu, Y.-N.; Fang, G.-S.; Kang, H.-J.; Gu, Y.; Tian, S.-K. Org. Biomol. Chem. 2015, 13, 5367.
[33] Li, M.-B.; Li, H.; Wang, J.; Liu, C.-R.; Tian, S.-K. Chem. Commun. 2013, 49, 8190.
[34] Liu, C.-R.; Li, M.-B.; Yang, C.-F.; Tian, S.-K. Chem.-Eur. J. 2009, 15, 793.
[35] Wu, X.-S.; Tian, S.-K. Chem. Commun. 2012, 48, 898.
[36] Yang, W.; Long, Y.; Zhang, S.; Zeng, Y.; Cai, Q. Org. Lett. 2013, 15, 3598.
[37] Narine, A. A.; Toulgoat, F.; Bisschops, T.; Enders, D. Angew. Chem., Int. Ed. 2008, 47, 5661.
[38] Reznichenko, A. L.; Hampel, F.; Hultzsch, K. C. Chem.-Eur. J. 2009, 15, 12819.
[39] Li, G.-Q.; Li, Y.; Dai, L.-X.; You, S.-L. Adv. Synth. Catal. 2008, 350, 1258.
[40] Dong, S.; Liu, X.; Zhu, Y.; He, P.; Lin, L.; Feng, X. J. Am. Chem. Soc. 2013, 135, 10026.
[41] Wang, M.; Huang, Z.; Xu, J.; Chi, Y. R. J. Am. Chem. Soc. 2014, 136, 1214.
[42] Minato, M.; Arimoto, H.; Nagasue, Y.; Demizu, Y.; Onomura, O. Tetrahedron 2008, 64, 6675.
[43] Minato, D.; Nagasue, Y.; Demizu, Y.; Onomura, O. Angew. Chem., Int. Ed. 2008, 47, 9458.
[44] Sibi, M. P.; Kawashima, K.; Stanley, L. M. Org. Lett. 2009, 11, 3894.
[45] Kong, D.; Han, S.; Wang, R.; Li, M.; Zi, G.; Hou, G. Chem. Sci. 2017, 8, 4558.
[46] Cochrane, E. J.; Leonori, D.; Hassallb, L. A.; Coldham, I. Chem. Commun. 2014, 50, 9910.
[47] Lei, B.-L.; Zhang, Q.-S.; Yu, W.-H.; Ding, Q.-P.; Ding, C.-H.; Hou, X.-L. Org. Lett. 2014, 16, 1944.
[48] Xiao, K.-J.; Chu, L.; Chen, G.; Yu, G.-Q. J. Am. Chem. Soc. 2016, 138, 7796.
[49] Zou, X.; Zhao, H.; Li, Y.; Gao, Q.; Ke, Z.; Xu, S. J. Am. Chem. Soc. 2019, 141, 5334.
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