Chinese Journal of Organic Chemistry >
Recent Progress in Upgrading of Alcohol and Amine via Asymmetric Dehydrogenative Coupling
Received date: 2022-07-02
Revised date: 2022-07-29
Online published: 2022-08-18
Supported by
National Key Research and Development Program of China(2021YFF0701600); National Natural Science Foundation of China(21871288); National Natural Science Foundation of China(21821002); National Natural Science Foundation of China(22171280); Science and Technology Commission of Shanghai Municipality(22XD1424900)
Chiral alcohol and amine are ubiquitous in natural products and pharmaceutically relevant molecules. Thus, developing the asymmetric synthesis of these molecules is of great importance. Compared with traditional methods, transition-metal-catalyzed asymmetric dehydrogenative coupling of alcohol and amine to advanced chiral alcohol and amine has been widely studied due to its excellent step-, atom- and redox-economy. This method allows for the one-step synthesis of structurally diverse chiral alcohol and chiral amine compounds from simple starting materials. Various types of asymmetric dehydrogenative coupling upgrading reactions involving alcohols and amines according to the types of coupling reagents are summarized and the outlook on the development of the field is provided.
Binyang Jiang , Shi-Liang Shi . Recent Progress in Upgrading of Alcohol and Amine via Asymmetric Dehydrogenative Coupling[J]. Chinese Journal of Organic Chemistry, 2022 , 42(10) : 3263 -3279 . DOI: 10.6023/cjoc202207002
| [1] | (a) Müller, C. E.; Schreiner, P. R. Angew. Chem., Int. Ed. 2011, 50, 6012. |
| [1] | (b) Krasnov, V. P.; Gruzdev, D. A.; Levit, G. L. Eur. J. Org. Chem. 2012, 1471. |
| [2] | (a) Fleury-Brégeot, N.; de la Fuente, V.; Castillón, S.; Claver, C. ChemCatChem 2010, 2, 1346. |
| [2] | (b) Cabré, A.; Verdaguer, X.; Riera, A. Chem. Rev. 2022, 122, 269. |
| [2] | (c) Noyori, R.; Ohkuma, T. Angew. Chem., Int. Ed. 2001, 40, 40. |
| [2] | (d) Ikariya, T.; Blacker, A. J. Acc. Chem. Res. 2007, 40, 1300. |
| [2] | (e) Malacea, R.; Poli, R.; Manoury, E. Coord. Chem. Rev. 2010, 254, 729. |
| [3] | (a) Liu, Y.-L.; Lin, X.-T. Adv. Synth. Catal. 2019, 361, 876. |
| [3] | (b) Bartlett, S. L.; Johnson, J. S. Acc. Chem. Res. 2017, 50, 2284. |
| [3] | (c) Shibasaki, M.; Kanai, M. Chem. Rev. 2008, 108, 2853. |
| [3] | (d) Riant, O.; Hannedouche, J. Org. Biomol. Chem. 2007, 5, 873. |
| [3] | (e) Kobayashi, S.; Mori, Y.; Fossey, J. S.; Salter, M. M. Chem. Rev. 2011, 111, 2626. |
| [4] | (a) Dobereiner, G. E.; Crabtree, R. H. Chem. Rev. 2010, 110, 681. |
| [4] | (b) Zhang, S.-Y.; Zhang, F.-M.; Tu, Y.-Q. Chem. Soc. Rev. 2011, 40, 1937. |
| [4] | (c) Cai, Y.; Li, F.; Li, Y.-Q.; Zhang, W.-B.; Liu, F.; Shi, S.-L. Tetrahedron Lett. 2018, 59, 1073. |
| [4] | (d) Campos, K. R. Chem. Soc. Rev. 2007, 36, 1069. |
| [4] | (e) Guillena, G.; Ramón D. J. Hydrogen Transfer Reactions, Springer, Switzerland, 2016. |
| [4] | (f) Kim, S. W.; Zhang, W.; Krische, M. J. Acc. Chem. Res. 2017, 50, 2371. |
| [4] | (g) Santana, C. G.; Krische, M. J. ACS Catal. 2021, 11, 5572. |
| [5] | Nakai, K.; Yoshida, Y.; Kurahashi, T.; Matsubara, S. J. Am. Chem. Soc. 2014, 136, 7797. |
| [6] | (a) Hassan, A.; Montgomery, T. P.; Krische, M. J. Chem. Commun. 2012, 48, 4692. |
| [6] | (b) Tsutsumi, R.; Hong, S.; Krische, M. J. Chem.-Eur. J. 2015, 21, 12903. |
| [6] | (c) Isbrandt, E. S.; Nasim, A.; Zhao, K.; Newman, S. G. J. Am. Chem. Soc. 2021, 143, 14646. |
| [7] | (a) Bower, J. F.; Skucas, E.; Patman, R. L.; Krische, M. J. J. Am. Chem. Soc. 2007, 129, 15134. |
| [7] | (b) Patman, R. L.; Williams, V. M.; Bower, J. F.; Krische, M. J. Angew. Chem., Int. Ed. 2008, 47, 5220. |
| [7] | (c) Shibahara, F.; Bower, J. F.; Krische, M. J. J. Am. Chem. Soc. 2008, 130, 14120. |
| [7] | (d) Williams, V. M.; Leung, J. C.; Patman, R. L.; Krische, M. J. Tetrahedron 2009, 65, 5024. |
| [8] | Maekawa, T.; Sekizawa, H.; Itami, K. Angew. Chem., Int. Ed. 2011, 50, 7022. |
| [9] | (a) Denmark, S. E.; Fu, J. Chem. Rev. 2003, 103, 2763. |
| [9] | (b) Kennedy, J. W. J.; Hall, D. G. Angew. Chem., Int. Ed. 2003, 42, 4732. |
| [10] | (a) Kimura, M.; Shimizu, M.; Shibata, K.; Tazoe, M.; Tamaru, Y. Angew. Chem., Int. Ed. 2003, 42, 3392. |
| [10] | (b) Zanoni, G.; Gladiali, S.; Marchetti, A.; Piccinini, P.; Tredici, I.; Vidari, G. Angew. Chem., Int. Ed. 2004, 43, 846. |
| [11] | Kim, I. S.; Ngai, M.-Y.; Krische, M. J. J. Am. Chem. Soc. 2008, 130, 6340. |
| [12] | Shu, C.; Hartwig, J. F. Angew. Chem., Int. Ed. 2004, 43, 4794. |
| [13] | Kim, I. S.; Ngai, M.-Y.; Krische, M. J. J. Am. Chem. Soc. 2008, 130, 14891. |
| [14] | (a) Hassan, A.; Townsend, I. A.; Krische, M. J. Chem. Commun. 2011, 47, 10028. |
| [14] | (b) Luo, G.; Xiang, M.; Krische, M. J. Org. Lett. 2019, 21, 2493. |
| [15] | (a) Montgomery, T. P.; Hassan, A.; Park, B. Y.; Krische, M. J. J. Am. Chem. Soc. 2012, 134, 11100. |
| [15] | (b) Xiang, M.; Luo, G.; Wang, Y.; Krische, M. J. Chem. Commun. 2019, 55, 981. |
| [15] | (c) Hassan, A.; Zbieg, J. R.; Krische, M. J. Angew. Chem., Int. Ed. 2011, 50, 3493. |
| [16] | Cabrera, J. M.; Krische, M. J. Angew. Chem., Int. Ed. 2019, 58, 10718. |
| [17] | Kim, I. S.; Han, S. B.; Krische, M. J. J. Am. Chem. Soc. 2009, 131, 2514. |
| [18] | Gao, X.; Zhang, Y. J.; Krische, M. J. Angew. Chem., Int. Ed. 2011, 50, 4173. |
| [19] | Han, S. B.; Gao, X.; Krische, M. J. J. Am. Chem. Soc. 2010, 132, 9153. |
| [20] | Zhang, Y. J.; Yang, J. H.; Kim, S. H.; Krische, M. J. J. Am. Chem. Soc. 2010, 132, 4562. |
| [21] | Feng, J.; Garza, V. J.; Krische, M. J. J. Am. Chem. Soc. 2014, 136, 8911. |
| [22] | Guo, Y.-A.; Lee, W.; Krische, M. J. Chem.-Eur. J. 2017, 23, 2557. |
| [23] | Feng, J.; Noack, F.; Krische, M. J. J. Am. Chem. Soc. 2016, 138, 12364. |
| [24] | Wang, G.; Franke, J.; Ngo, C. Q.; Krische, M. J. J. Am. Chem. Soc. 2015, 137, 7915. |
| [25] | Taylor, R. D.; MacCoss, M.; Lawson, A. D. G. J. Med. Chem. 2017, 60, 1638. |
| [26] | Woo, S. K.; Geary, L. M.; Krische, M. J. Angew. Chem., Int. Ed. 2012, 51, 7830. |
| [27] | Liang, T.; Woo, S. K.; Krische, M. J. Angew. Chem., Int. Ed. 2016, 55, 9207. |
| [28] | Liang, T.; Nguyen, K. D.; Zhang, W.; Krische, M. J. J. Am. Chem. Soc. 2015, 137, 3161. |
| [29] | Gellrich, U.; Meißner, A.; Steffani, A.; Ka? hny, M.; Drexler, H.-J.; |
| [30] | Heller, D.; Plattner, D. A.; Breit, B. J. Am. Chem. Soc. 2014, 136, 1097. |
| [31] | Park, B. Y.; Nguyen, K. D.; Chaulagain, M. R.; Komanduri, V.; Krische, M. J. J. Am. Chem. Soc. 2014, 136, 11902. |
| [32] | Xiang, M.; Ghosh, A.; Krische, M. J. J. Am. Chem. Soc. 2021, 143, 2838. |
| [33] | Ortiz, E.; Chang, Y.-H.; Shezaf, J. Z.; Shen, W.; Krische, M. J. J. Am. Chem. Soc. 2022, 144, 8861. |
| [34] | Liang, T.; Zhang, W.; Krische, M. J. J. Am. Chem. Soc. 2015, 137, 16024. |
| [35] | Cai, Y.; Zhang, J.-W.; Li, F.; Liu, J.-M.; Shi, S.-L. ACS Catal. 2019, 9, 1. |
| [36] | Ho, C.-Y.; Jamison, T. F. Angew. Chem., Int. Ed. 2007, 46, 782. |
| [37] | Zbieg, J. R.; Moran, J.; Krische, M. J. J. Am. Chem. Soc. 2011, 133, 10582. |
| [38] | Zbieg, J. R.; Yamaguchi, E.; McInturff, E. L.; Krische, M. J. Science 2012, 336, 324. |
| [39] | McInturff, E. L.; Yamaguchi, E.; Krische, M. J. J. Am. Chem. Soc. 2012, 134, 20628. |
| [40] | Han, S. B.; Kim, I. S.; Han, H.; Krische, M. J. J. Am. Chem. Soc. 2009, 131, 6916. |
| [41] | Spielmann, K.; Xiang, M.; Schwartz, L. A.; Krische, M. J. J. Am. Chem. Soc. 2019, 141, 14136. |
| [42] | Xiang, M.; Pfaffinger, D. E.; Ortiz, E.; Brito, G. A.; Krische, M. J. J. Am. Chem. Soc. 2021, 143, 8849. |
| [43] | Geary, L. M.; Woo, S. K.; Leung, J. C.; Krische, M. J. Angew. Chem., Int. Ed. 2012, 51, 2972. |
| [44] | Nguyen, K. D.; Herkommer, D.; Krische, M. J. J. Am. Chem. Soc. 2016, 138, 5238. |
| [45] | (a) Suzuki, A. Angew. Chem., Int. Ed. 2011, 50, 6722. |
| [45] | (b) Fyfe, J. W. B.; Watson, A. J. B. Chem 2017, 3, 31. |
| [46] | (a) Duan, H.-F.; Xie, J.-H.; Shi, W.-J.; Zhang, Q.; Zhou, Q.-L. Org. Lett. 2006, 1479. |
| [46] | (b) Tomita, D.; Kanai, M.; Shibasaki, M. Chem.-Asian. J. 2006, 1, 161. |
| [46] | (c) Duan, H.-F.; Xie, J.-H.; Qiao, X.-C.; Wang, L.-X.; Zhou, Q.-L. Angew. Chem., Int. Ed. 2008, 47, 4351. |
| [46] | (d) Li, R.; Luo, K.; Hu, Y.; Tang, W. Adv. Synth. Catal. 2013, 355, 1297. |
| [46] | (e) Shintani, R.; Inoue, M.; Hayashi, T. Angew. Chem., Int. Ed. 2006, 45, 3353. |
| [47] | Casnati, A.; Lichosyt, D.; Lainer, B.; Veth, L.; Dydio, P. Org. Lett. 2021, 23, 3502. |
| [48] | Cai, Y.; Shi, S.-L. J. Am. Chem. Soc. 2021, 143, 11963. |
| [49] | (a) Cai, Y.; Ruan, L.-X.; Rahman, A.; Shi, S.-L. Angew. Chem., Int. Ed. 2021, 60, 5262. |
| [49] | (b) Cai, Y.; Yang, X.-T.; Zhang, S.-Q.; Li, F.; Li, Y.-Q.; Ruan, L.-X.; Hong, X.; Shi, S.-L. Angew. Chem., Int. Ed. 2018, 57, 1376. |
| [49] | (c) Zhang, W.-B.; Yang, X.-T.; Ma, J.-B.; Su, Z.-M.; Shi, S.-L. J. Am. Chem. Soc. 2019, 141, 5628. |
| [49] | (d) Cai, Y.; Ye, X.; Liu, S.; Shi, S.-L. Angew. Chem., Int. Ed. 2019, 58, 13433. |
| [49] | (e) Shen, D.; Zhang, W.-B.; Li, Z.; Shi, S.-L.; Xu, Y. Adv. Synth. Catal. 2020, 362, 112. |
| [49] | (f) Li, Y.-Q.; Li, F.; Shi, S.-L. Chin. J. Chem. 2020, 38, 1035. |
| [49] | (g) Wang, Z.-C.; Gao, J.; Cai, Y.; Ye, X.; Shi, S.-L. CCS Chem. 2022, 4, 1169. |
| [49] | (h) Ma, J.-B.; Zhao, X.; Zhang, D.; Shi, S.-L. J. Am. Chem. Soc. 2022, 144, 13643. |
| [50] | Moran, J.; Smith, A. G.; Carris, R. M.; Johnson, J. S.; Krische, M. J. J. Am. Chem. Soc. 2011, 133, 18618. |
| [51] | Ambler, B. R.; Turnbull, B. W. H.; Suravarapu, S. R.; Uteuliyev, M. M.; Huynh, N. O.; Krische, M. J. J. Am. Chem. Soc. 2018, 140, 9091. |
| [52] | Bender, M.; Turnbull, B. W. H.; Ambler, B. R.; Krische, M. J. Science 2017, 357, 779. |
| [53] | Wang, K.; Zhang, L.; Tang, W.; Sun, H.; Xue, D.; Lei, M.; Xiao, J.; Wang, C. Angew. Chem., Int. Ed. 2020, 59, 11408. |
| [54] | Ng, T. W.; Liao, G.; Lau, K. K.; Pan, H.-J.; Zhao, Y. Angew. Chem., Int. Ed. 2020, 59, 11384. |
| [55] | (a) Xu, R.; Wang, K.; Liu, H.; Tang, W.; Sun, H.; Xue, D.; Xiao, J.; Wang, C. Angew. Chem., Int. Ed. 2020, 59, 21959. |
| [55] | (b) Zhang, X.; Ma, W.; Zhang, J.; Tang, W.; Xue, D.; Xiao, J.; Sun, H.; Wang, C. Angew. Chem., Int. Ed. 2022, 61, e202203244. |
| [55] | (c) Li, F.; Long, L.; He, Y.-M.; Li, Z.; Chen, H.; Fan, Q. H. Angew. Chem., Int. Ed. 2022, 61, e202202972. |
| [56] | Pan, S.; Endo, K.; Shibata, T. Org. Lett. 2011, 13, 4692. |
| [57] | Jain, P.; Verma, P.; Xia, G.; Yu, J.-Q. Nat. Chem. 2017, 9, 140. |
| [58] | Bergonzini, G.; Schindler, C. S.; Wallentin, C.-J.; Jacobsen, E. N.; Stephenson, C. R. J. Chem. Sci. 2014, 5, 112. |
| [59] | (a) Herzon, S. B.; Hartwig, J. F. J. Am. Chem. Soc. 2007, 129, 6690. |
| [59] | (b) Kubiak, R.; Prochnow, I.; Doye, S. Angew. Chem., Int. Ed. 2009, 48, 1153. |
| [59] | (c) Reznichenko, A. L.; Hultzsch, K. C. J. Am. Chem. Soc. 2012, 134, 3300. |
| [59] | (d) Koperniku, A.; Foth, P. J.; Sammis, G. M.; Schafer, L. L. J. Am. Chem. Soc. 2019, 141, 18944. |
| [59] | (e) Bahena, E. N.; Griffin, S. E.; Schafer, L. L. J. Am. Chem. Soc. 2020, 142, 20566. |
| [59] | (f) Yao, W.-W.; Li, R.; Chen, H.; Chen, M.-K.; Luan, Y.-X.; Wang, Y.; Yu, Z.-X.; Ye, M. Nat. Commun. 2021, 12, 3800. |
| [60] | Eisenberger, P.; Ayinla, R. O.; Lauzon, J. M. P.; Schafer, L. L. Angew. Chem., Int. Ed. 2009, 48, 8361. |
| [61] | Li, Y.; Liu, Y.-C.; Shi, H. J. Am. Chem. Soc. 2021, 143, 4154. |
| [62] | Yan, X.-B.; Li, Y.; Wu, W.-Q.; Xu, L.; Li, K.; Liu, Y.-C.; Shi, H. Nat. Commun. 2021, 12, 5881. |
/
| 〈 |
|
〉 |
