Progresses in the Application of Kinetic Resolution in Transition Metal Catalyzed Asymmetric (Transfer) Hydrogenation

  • Yangyang Chu ,
  • Zhaobin Han ,
  • Kuiling Ding
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  • a School of Materials and Chemistry, University of Shanghai for Science and Technology, Shanghai 200093
    b State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032
    c School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai 200240
    d Frontiers Science Center for Transformative Molecules, Shanghai Jiao Tong University, Shanghai 200240

Received date: 2023-03-01

  Revised date: 2023-04-08

  Online published: 2023-04-26

Supported by

National Key R&D Program of China(2021YFA1500200); National Natural Science Foundation of China(21872167); Program of Shanghai Academic/Technology Research Leader(22XD1424800)

Abstract

Kinetic resolution (KR) has long been a popular and classical strategy in organic synthesis to obtain optically active compounds from racemic substrates, and transition metal catalyzed asymmetric (transfer) hydrogenation is a powerful method for the synthesis of chiral compounds with high efficiency and atom economy. Over the years, a large variety of unsaturated compounds bearing different types of chiral centers have been kinetically resolved with great efficiency via asymmetric (transfer) hydrogenation using some well-established chiral transition metal catalysts, and KR has been demonstrated to be a versatile technique in the synthesis of various chiral intermediates for biologically active compounds and natural products. The research progresses in this field are summarized. Moreover, the prospects of further developments are also discussed.

Cite this article

Yangyang Chu , Zhaobin Han , Kuiling Ding . Progresses in the Application of Kinetic Resolution in Transition Metal Catalyzed Asymmetric (Transfer) Hydrogenation[J]. Chinese Journal of Organic Chemistry, 2023 , 43(6) : 1934 -1951 . DOI: 10.6023/cjoc202303001

References

[1]
Ojima, I. Catalytic Asymmetric Synthesis, 3rd ed., Wiley, Hoboken, 2010.
[2]
(a) Moss, G. P. Pure Appl. Chem. 1996, 68, 2193.
[2]
(b) Keith, J. M.; Larrow, J. F.; Jacobsen, E. N. Adv. Synth. Catal. 2001, 343, 5.
[2]
(c) Vedejs, E.; Jure, M. Angew. Chem., nt. Ed. 2005, 44, 3974.
[2]
(d) Pellissier, H. Adv. Synth. Catal. 2011, 353, 1613.
[2]
(e) Su, N.; Zhang, F.; Gong, Y. Chin. J. Org. Chem. 2007, 27, 1345. (in Chinese)
[2]
(苏宁, 张方林, 龚跃法, 有机化学, 2007, 27, 1345.)
[3]
Kagan, H. B.; Fiaud, J. C. Top. Stereochem. 1988, 18, 249.
[4]
Bhat, V.; Welin, E. R.; Guo, X.; Stoltz, B. M. Chem. Rev. 2017, 117, 4528.
[5]
Vedejs, E.; Chen, X. J. Am. Chem. Soc. 1997, 119, 2584.
[6]
(a) de Vries, J. G.; Elsevier, C. J. Handbook of Homogeneous Hydrogenation, Vol. 1-3, Wiley, Weinheim, 2010.
[6]
(b) Tang, W.; Zhang, X. Chem. Rev. 2003, 103, 3029.
[6]
(c) Xie, J.-H.; Zhu, S.-F.; Zhou, Q.-L. Chem. Rev. 2011, 111, 1713.
[6]
(d) Wang, D.-S.; Chen, Q.-A.; Lu, S.-M.; Zhou, Y.-G. Chem. Rev. 2012, 112, 2557.
[6]
(e) Zhang, Z.; Butt, N. A.; Zhang, W. Chem. Rev. 2016, 116, 14769.
[6]
(f) Zhang, Z.; Butt, N. A.; Zhou, M.; Liu, D.; Zhang, W. Chin. J. Chem. 2018, 36, 443,
[6]
(g) Mu, B.-S.; Zhang, Z.-H.; Wu, W.-B.; Yu, J.-S.; Zhou, J. Acta Chim. Sinica 2021, 79, 685. (in Chinese)
[6]
(穆博帅, 张志豪, 武文彪, 余金生, 周剑, 化学学报, 2021, 79, 685.)
[6]
(h) Shang, Y.; Xiao, J.; Wang, Y.; Peng, Y. Acta Chim. Sinica 2021, 79, 1303. (in Chinese)
[6]
(尚阳, 肖检, 王雅雯, 彭羽, 化学学报, 2021, 79, 1303.)
[7]
El-Baba, S.; Poulin, J.-C.; Kagan, H. B. Tetrahedron 1984, 40, 4275.
[8]
Wei, Y.; Shi, M. Chem. Rev. 2013, 113, 6659.
[9]
Brown, J. M.; Cutting, I. J. Chem. Soc., hem. Commun. 1985, 578.
[10]
Ando, D.; Bevan, C.; Brown, J. M.; Price, D. W. J. Chem. Soc., hem. Commun. 1992, 592.
[11]
Brown, J. M.; James, A. P.; Prior, L. M. Tetrahedron Lett. 1987, 28, 2179.
[12]
(a) Brown, J. M. Angew. Chem.,Int. Ed. 1987, 26, 190.
[12]
(b) Brown, J. M.; Cutting, I.; James, A. P. Bull. Soc. Chim. Fr. 1988, 211.
[13]
Leitner, W.; Brown, J. M.; Brunner, H. J. Am. Chem. Soc. 1993, 115, 152.
[14]
Holz, J.; Sch?ffner, B.; Zayas, O.; Spannenberg, A.; B?rner, A. Adv. Synth. Catal. 2008, 350, 2533.
[15]
(a) Trost, B. M.; Rao, M. Angew. Chem.,Int. Ed. 2015, 54, 5026.
[15]
(b) Otocka, S.; Kwiatkowska, M.; Madalińska, L.; Kie?basiński, P. Chem. Rev. 2017, 117, 4147.
[16]
(a) Bentley, R. Chem. Soc. Rev. 2005, 34, 609.
[16]
(b) Legros, J.; Dehli, J. R.; Bolm, C. Adv. Synth. Catal. 2005, 347, 19.
[17]
(a) Mikolajczyk, M.; Drabowicz, J. Phosphrous, Sulfur Silicon Relat. Elem. 1976, 1, 301.
[17]
(b) Annunziata, R.; Borgogno, G.; Montanari, F.; Quici, S.; Cucinella, S. J. Chem. Soc., erkin Trans. 1 1981, 113.
[18]
Lao, J. R.; Fernández-Pérez, H.; Vidal-Ferran, A. Org. Lett. 2015, 17, 4114.
[19]
Fernández-Pérez, H.; Lao, J. R.; Grabulosa, A.; Vidal-Ferran, A. Eur. J. Org. Chem. 2020, 2020, 4331.
[20]
Dutartre, M.; Bayardon, J.; Jugé, S. Chem. Soc. Rev. 2016, 45, 5771.
[21]
Fernández-Pérez, H.; Vidal-Ferran, A. Org. Lett. 2019, 21, 7019.
[22]
Buffat, M. G. P. Tetrahedron 2004, 60, 1701.
[23]
Zhou, C.-X.; Zhang, W.; You, S.-L. Angew. Chem., nt. Ed. 2012, 51, 12662.
[24]
Li, W.; Yang, H.; Li, R.; Lv, H.; Zhang, X. ACS Catal. 2020, 10, 2603.
[25]
(a) Kitamura, M.; Kasahara, I.; Manabe, K.; Noyori, R.; Takaya, H. J. Org.Chem. 1998, 53, 710.
[25]
(b) Mikami, K.; Yusa, Y.; Korenaga, T. Org. Lett. 2002, 1643.
[26]
Wu, H.; Margarita, C.; Jongcharoenkamol, J.; Nolan, M. D.; Singh, T.; Andersson, P. G. Chem. Sci. 2021, 12, 1937.
[27]
Wiesenfeldt, M. P.; Nairoukh, Z.; Dalton, T.; Glorius, F. Angew. Chem., nt. Ed. 2019, 58, 10460.
[28]
Ding, Y.-X.; Zhu, Z.-H.; Chen, M.-W.; Yu, C.-B.; Zhou, Y.-G. Angew. Chem., nt. Ed. 2022, 61, e202205623.
[29]
Veitch, N. C.; Grayer, R. J. Nat. Prod. Rep. 2011, 28, 1626.
[30]
(a) Noyori, R.; Ohkuma, T. Angew. Chem., nt. Ed. 2001, 40, 40.
[30]
(b) Xie, J.-H.; Bao, D.-H.; Zhou, Q.-L. Synthesis 2015, 47, 460.
[31]
Lemke, M.-K.; Schwab, P.; Fischer, P.; Tischer, S.; Witt, M.; Noehringer, L.; Rogachev, V.; J?ger, A.; Kataeva, O.; Fr?hlich, R.; Metz, P. Angew. Chem., nt. Ed. 2013, 52, 11651.
[32]
Ke?berg, A.; Metz, P. Angew. Chem., nt. Ed. 2016, 55, 1160.
[33]
Ke?berg, A.; Metz, P. Org. Lett. 2016, 18, 6500.
[34]
He, B.; Phansavath, P.; Ratovelomanana-Vidal, V. Org. Chem. Front. 2021, 8, 2504.
[35]
Zhu, Y.; Zhou, J.; Li, J.; Xu, K.; Ye, J.; Lu, Y.; Liu, D.; Zhang, W. Org. Chem. Front. 2021, 8, 6609.
[36]
Park, S.; Lee, H.-K. RSC Adv. 2021, 11, 23161.
[37]
(a) Mu?ller, C. E.; Schreiner, P. R. Angew. Chem., nt. Ed. 2011, 50, 6012.
[37]
(b) Sigman, M. S.; Jensen, D. R. Acc. Chem. Res. 2006, 39, 221.
[38]
(a) Yang, X.-H.; Wang, K.; Zhu, S.-F.; Xie, J.-H.; Zhou, Q.-L. J. Am. Chem. Soc. 2014, 136, 17426.
[38]
(b) Yang, X.-H.; Gu, X.-S.; Bin, H.-Y.; Xie, J.-H.; Zhou, Q.-L. Chin. J. Org. Chem. 2020, 40, 3963. (in Chinese)
[38]
(杨小会, 顾雪松, 宾怀玉, 谢建华, 周其林, 有机化学, 2020, 40, 3963.)
[39]
Dai, L.-X.; Hou, X.-L. Chiral Ferrocenes in Asymmetric Catalysis, Wiley, Weinheim, 2010.
[40]
Liu, C.-X.; Zhao, F.; Feng, Z.; Wang, Q.; Gu, Q.; You, S.-L. Nat. Synth. 2023, 2, 49.
[41]
Liu, R.; Zhou, G.; Hall, T. H.; Clarkson, G. J.; Wills, M.; Chen, W. Adv. Synth. Catal. 2015, 357, 3453.
[42]
Delcourt, M.-L.; Turcaud, S.; Benedetti, E.; Micouin, L. Adv. Synth. Catal. 2016, 358, 1213.
[43]
Delcourt, M.-L.; Felder, S.; Turcaud, S.; Pollok, C. H.; Merten, C.; Benedetti, E.; Micouin, L. J. Org. Chem. 2019, 84, 5369.
[44]
Nugent, T. C. Chiral Amine Synthesis, Wiley, Weinheim, 2010.
[45]
Lensink, C.; de Vries, J. G. Tetrahedron: Asymmetry 1993, 4, 215.
[46]
Viso, A.; Lee, N. E.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 9373.
[47]
Yang, Z.; Chen, F.; He, Y.; Yang, N.; Fan, Q.-H. Angew. Chem., nt. Ed. 2016, 55, 13863.
[48]
Liu, C.; Wang, M.; Xu, Y.; Li, Y.; Liu, Q. Angew. Chem., nt. Ed. 2022, 61, e202202814.
[49]
Zhao, Y.; Ding, Y.-X.; Wu, B.; Zhou, Y.-G. J. Org. Chem. 2021, 86, 10788.
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