综述与进展

过渡金属催化的不对称氢酰化反应研究进展

  • 王豪锐 ,
  • 叶萌春
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  • 南开大学化学学院 元素有机化学国家重点实验室 天津 300071

收稿日期: 2022-07-26

  修回日期: 2022-10-05

  网络出版日期: 2022-10-10

基金资助

国家自然科学基金(21871145); 国家自然科学基金(22188101); 可持续化学转化海河实验室和南开大学新物质科学中心(63181206)

Research Advance on Enantioselective Transition Metal-Catalyzed Hydroacylation Reactions

  • Haorui Wang ,
  • Mengchun Ye
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  • State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071
* Corresponding author. E-mail:

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)

摘要

过渡金属催化醛和π-不饱和键的氢酰化反应具有原料来源广泛、价廉易得的优点, 且具有高的原子和步骤经济性, 为C—C键的构筑提供了一条经济而高效的途径. 因此, 近几十年来, 该反应受到了持续而广泛的关注. 此篇综述将对过渡金属催化的不对称氢酰化反应的研究进展进行总结, 详细阐述反应类型、不对称控制方法和反应机理等.

本文引用格式

王豪锐 , 叶萌春 . 过渡金属催化的不对称氢酰化反应研究进展[J]. 有机化学, 2022 , 42(10) : 3152 -3166 . DOI: 10.6023/cjoc202207036

Abstract

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.

参考文献

[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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