Chinese Journal of Organic Chemistry >
Progresses in the Application of Kinetic Resolution in Transition Metal Catalyzed Asymmetric (Transfer) Hydrogenation
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)
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.
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
| [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. |
/
| 〈 |
|
〉 |