Chinese Journal of Organic Chemistry >
Research Advance on Enantioselective Transition Metal-Catalyzed Hydroacylation Reactions
Received date: 2022-07-26
Revised date: 2022-10-05
Online published: 2022-10-10
Supported by
National Natural Science Foundation of China(21871145); National Natural Science Foundation of China(22188101); Haihe Laboratory of Sustainable Chemical Transformations and the “Frontiers Science Center for New Organic Matter”, Nankai University(63181206)
Transition metal-catalyzed hydroacylation reaction of aldehydes with π-unsaturated compounds provides an economical and efficient method for the construction of C—C bonds, not only allowing readily available starting materials to be used as substrates, but also featuring high atom and step economy. Therefore, the reaction has received continuous and extensive attention during the past several decades. The advances on enantioselective transition metal-catalyzed hydroacylation reactions are summarized, focusing on reaction types, asymmetric strategies and reaction mechanisms.
Key words： transition metal catalysis; hydroacylation; asymmetric catalysis; aldehydes; alkenes
Haorui Wang , Mengchun Ye . Research Advance on Enantioselective Transition Metal-Catalyzed Hydroacylation Reactions[J]. Chinese Journal of Organic Chemistry, 2022 , 42(10) : 3152 -3166 . DOI: 10.6023/cjoc202207036
| [1] | (a) Gandeepan, P.; Müller, T.; Zell, D.; Cera, G.; Warratz, S.; Ackermann, L. Chem. Rev. 2019, 119, 4, 2192. |
| [1] | (b) Qiu, Y.; Zhu, C.; Stangier, M.; Struwe, J.; Ackermann, L. CCS Chem. 2020, 2, 1529. |
| [1] | (c) Tong, H.-R.; Li, B.; Li, G.; He, G.; Chen, G. CCS Chem. 2021, 3, 1797. |
| [1] | (d) Li, J.-F.; Luan, Y.-X.; Ye, M. Sci. China Chem. 2021, 64, 1923. |
| [1] | (e) Tao, P.; Jia, Y. Sci. China Chem. 2016, 59, 1109. |
| [2] | For selected examples on other types of couplings of π-unsaturated compounds with aldehydes, see: (a) Zheng, Y.-L.; Ye, M. Chin. J. Chem. 2020, 38, 489. |
| [2] | (b) Han, X.-W.; Zhang, T.; Yao, W.-W.; Chen, H.; Ye, M. CCS Chem. 2020, 2, 955. |
| [2] | (c) Han, X.-W.; Zhang, T.; Zheng, Y.-L.; Yao, W.-W.; Li, J.-F.; Pu, Y.-G.; Ye, M.; Zhou, Q.-L. Angew. Chem., Int. Ed. 2018, 57, 5068. |
| [2] | (d) Zheng, Y.-L.; Luan, Y.-X.; Ye, M. Synlett 2016, 27, 2401. |
| [3] | For selected reviews about hydroaclytion: (a) Christmann, M. Angew. Chem., Int. Ed. 2005, 44, 2632. |
| [3] | (b) Jun, C.-H.; Jo, E.-A.; Park, J.-W. Eur. J. Org. Chem. 2007, 12, 1869. |
| [3] | (c) Willis, M. C. Chem. Rev. 2010, 110, 725. |
| [3] | (d) DiRocco, D. A.; Rovis, T. Angew. Chem., Int. Ed. 2011, 50, 7982. |
| [3] | (e) Carlos, G.-R.; Willis, M. C. Pure Appl. Chem., 2011, 83, 577. |
| [3] | (f) Leung, J. C.; Krische, M. J. Chem. Sci. 2012, 3, 2202. |
| [3] | (g) Watsona, I. D. G.; Toste, F. D. Chem. Sci. 2012, 3, 2899. |
| [3] | (h) Murphy, S. K.; Bruch, A.; Dong, V. M. Angew. Chem., Int. Ed. 2014, 53, 2455. |
| [3] | (i) Murphy, S. K.; Dong, V. M. Chem. Commun. 2014, 50, 13645. |
| [3] | (j) Ghosh, A.; Johnson, K. F.; Vickerman, K. L.; Walker, J. A., Jr.; Stanley, L. M. Org. Chem. Front. 2016, 3, 639. |
| [3] | (k) Kim, D.-S.; Park, W.-J.; Jun, C.-H. Chem. Rev. 2017, 117, 8977. |
| [3] | (l) Davison, R. T.; Kuker, E. L.; Dong, V. M. Acc. Chem. Res. 2021, 54, 1236. |
| [4] | Sakai, K.; Ide, J.; Oda, O.; Nakamura, N. Tetrahedron Lett. 1972, 13, 1287. |
| [5] | James, B. R.; Young, C. G. J. Chem. Soc., Chem. Commun. 1983, 7, 59. |
| [6] | James, B. R.; Young, C. G. J. Organomet. Chem. 1985, 285, 321. |
| [7] | Taura, Y.; Tanaka, M.; Funakoshi, K.; Sakai, K. Tetrahedron Lett. 1989, 30, 6349. |
| [8] | Taura, Y.; Tanaka, M.; Wu, X.-M.; Funakoshi, K.; Sakai, K. Tetrahedron Lett. 1991, 47, 4879. |
| [9] | Wu, X.-M.; Funakoshi, K.; Sakai, K. Tetrahedron Lett. 1992, 33, 6331. |
| [10] | Barnhart, R. W.; Wang, X.; Noheda, P.; Bergens, S. H.; Whelan, J.; Bosnich, B. Tetrahedron 1994, 50, 4335. |
| [11] | Barnhart, R. W.; Wang, X.; Noheda, P.; Bergens, S. H.; Whelan, J.; Bosnich, B. J. Am. Chem. Soc. 1994, 116, 946. |
| [12] | Richard, W. B.; McMorran, D. A.; Bosnich, B. Chem. Commun. 1997, 589. |
| [13] | Wu, X.-M.; Funakoshi, K.; Sakai, K. Tetrahedron Lett. 1993, 34, 5927. |
| [14] | Tanaka, M.; Imai, M.; Fujio, M.; Sakamoto, E.; Takahashi, M.; Eto-Kato, Y.; Wu, X.-M.; Funakoshi, K.; Sakai, K.; Suemune, H. J. Org. Chem. 2000, 65, 5806. |
| [15] | Richard, W. B.; Bosnich, B. Organometallics. 1995, 14, 4343. |
| [16] | Fujio, M.; Tanaka, M.; Wu, X.-M.; Funakoshi, K.; Sakai, K.; Suemune, H. Chem. Lett. 1998, 881. |
| [17] | Imai, M.; Tanaka, M.; Suemune, H. Tetrahedron. 2001, 57, 1205. |
| [18] | Hoffman, T. J.; Carreira, E. M. Angew. Chem., Int. Ed. 2011, 50, 10670. |
| [19] | Park, J. W.; Kou, K. G. M.; Kim, D. K.; Dong, V. M. Chem. Sci. 2015, 6, 4479. |
| [20] | Kim, D. K.; Riedel, J.; Kim, R. S.; Dong, V. M. J. Am. Chem. Soc. 2017, 139, 10208. |
| [21] | Chen, Z.; Aota, Y.; Nguyen, H. M. H.; Dong, V. M. Angew. Chem., Int. Ed. 2019, 131, 4753. |
| [22] | Oonishi, Y.; Hosotani, A.; Yokoe, T.; Sato, Y. Org. Lett. 2019, 21, 4120. |
| [23] | Liu, C.; Yuan, J.; Zhang, Z.; Gridnev, I. D.; Zhang, W. Angew. Chem., Int. Ed. 2021, 60, 8997. |
| [24] | Tanaka, K.; Fu, G. C. J. Am. Chem. Soc. 2002, 124, 10296. |
| [25] | Tanaka, K.; Fu, G. C. J. Am. Chem. Soc. 2003, 125, 8078. |
| [26] | Wu, X.; Chen, Z.; Bai, Y.-B.; Dong, V. M. J. Am. Chem. Soc. 2016, 138, 12013. |
| [27] | Kundu, K.; McCullagh, J. V.; Morehead, A. T., Jr. J. Am. Chem. Soc. 2005, 127, 16042. |
| [28] | Phan, D. H. T.; Kim, B.; Dong, V. M. J. Am. Chem. Soc. 2009, 131, 15608. |
| [29] | Yang, J.; Yoshikai, N. J. Am. Chem. Soc. 2014, 136, 16748. |
| [30] | Ghosh, A.; Stanley, L. M. Chem. Commun. 2014, 50, 2765. |
| [31] | Vickerman, K. L.; Stanley, L. M. Org. Lett. 2017, 19, 5054. |
| [32] | Rastelli, E. J.; Truong, N. T.; Coltart, D. M. Org. Lett. 2016, 18, 5588. |
| [33] | Johnson, K. F.; Schneider, E. A.; Schumacher, B. P.; Ellern, A.; Scanlon, J. D.; Stanley, L. M. Chem. Eur. J. 2016, 22, 15619. |
| [34] | Yang, J.; Rérat, A.; Lim, Y. J.; Gosmini, C.; Yoshikai, N. Angew. Chem., Int. Ed. 2017, 129, 2489. |
| [35] | Yuan, J.; Liu, C.; Chen, Y.; Zhang, Z.; Yan, D.; Zhang, W. Tetrahedron 2019, 75, 269. |
| [36] | Shirai, T.; Iwasaki, T.; Kanemoto, K.; Yamamoto, Y. Chem. Asian J. 2020, 15, 1858. |
| [37] | Du, X. W.; Ghosh, A.; Stanley, L. M. Org. Lett. 2014, 16, 4036. |
| [38] | Johnson, K. F.; Schmidt, A. C.; Stanley, L. M. Org. Lett. 2015, 17, 4654. |
| [39] | Coulter, M. M.; Doman, P. K.; Dong, V. M. J. Am. Chem. Soc. 2009, 131, 6932. |
| [40] | Shen, Z.; Khan, H. A.; Dong, V. M. J. Am. Chem. Soc. 2008, 130, 2916. |
| [41] | Shen, Z.; Dornan, P. K.; Khan, H. A.; Woo, T. K.; Dong, V. M. J. Am. Chem. Soc. 2009, 131, 1077. |
| [42] | Khan, H. A.; Kou, K. G. M.; Dong, V. M. Chem. Sci. 2011, 2, 407. |
| [43] | Beletskiy, E. V.; Sudheer, C.; Douglas, C. J. J. Org. Chem. 2012, 77, 5884. |
| [44] | Vora, K. P.; Lochow, C. F.; Miller, R. G. J. Organomet. Chem. 1980, 192, 257. |
| [45] | Stemmler, R. T.; Bolm, C. Adv. Synth. Catal. 2007, 349, 1185. |
| [46] | Osborne, J. D.; Randell-Sly, H. E.; Currie, G. S.; Cowley, A. R.; Willis, M. C. J. Am. Chem. Soc. 2008, 130, 17232. |
| [47] | Coulter, M. M.; Kou, K. G. M.; Galligan, B.; Dong, V. M. J. Am. Chem. Soc. 2010, 132, 16330. |
| [48] | Phan, D. H. T.; Kou, K. G. M.; Dong, V. M. J. Am. Chem. Soc. 2010, 132, 16354. |
| [49] | Goetzke, F. W.; Siderab, M.; Fletcher, S. P. Chem. Sci. 2022, 13, 236 |
| [50] | Inui, Y.; Tanaka, M.; Imai, M.; Tanaka, K.; Suemune, H. Chem. Pharm. Bull. 2009, 57, 1158. |
| [51] | Shibata, Y.; Tanaka, K. J. Am. Chem. Soc. 2009, 131, 12552. |
| [52] | Kou, K. G. M.; Le, D. N.; Dong, V. M. J. Am. Chem. Soc. 2014, 136, 9471. |
| [53] | Kou, K. G. M.; Longobardi, L. E.; Dong, V. M. Adv. Synth. Catal. 2015, 357, 2233. |
| [54] | Whyte, A.; Bajohr, J.; Torelli, A.; Lautens, M. Angew. Chem., Int. Ed. 2020, 59, 16409. |
| [55] | Parsutkar, M. M.; RajanBabu T. V. J. Am. Chem. Soc. 2021, 143, 12825. |
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