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2023 , Vol. 43 >Issue 8: 2743 - 2763

DOI: https://doi.org/10.6023/cjoc202301005

综述与进展

羰基α-位胺化反应研究进展

  • 吴文倩 ,
  • 陈春霞 ,
  • 彭进松 ,
  • 李占宇
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  • 东北林业大学化学化工与资源利用学院 哈尔滨 150040

收稿日期: 2023-01-06

  修回日期: 2023-02-19

  网络出版日期: 2023-04-10

基金资助

黑龙江省自然科学基金(LH2022B003); 中央高校基本科研业务费专项资金(41421029); 中央高校基本科研业务费专项资金(2572020BU03)

收起

Research Progress of Carbonyl α-Position Amination

  • Wenqian Wu ,
  • Chunxia Chen ,
  • Jinsong Peng ,
  • Zhanyu Li
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  • College of Chemistry, Chemical Engineering and Resource Utilization, Northeast Forestry University, Harbin 150040
*E-mail: ;

Received date: 2023-01-06

  Revised date: 2023-02-19

  Online published: 2023-04-10

Supported by

The Natural Science Foundation of Heilongjiang Province(LH2022B003); The Fundamental Research Funds for the Central Universities(41421029); The Fundamental Research Funds for the Central Universities(2572020BU03)

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摘要

α-氨基羰基衍生物是一类重要分子骨架, 存在于许多药物分子和天然产物分子中; 同时, 也是一类重要的有机合成中间体, 用于合成许多重要的有机化合物分子. 发展简单、高效的方法合成结构多样性的α-氨基羰基衍生物具有重要的研究意义. 总结了近几十年来羰基α-位碳氢键的直接胺化反应, 根据反应所经历的不同活化模式, 对这类反应进行了分类总结, 主要分为亲电胺化、氧化胺化、卤化物介导的胺化和电化学胺化四类反应.

关键词： α-氨基酮; α-氨基醛; 羰基化合物; 亲电胺化; 氧化胺化

本文引用格式

吴文倩 , 陈春霞 , 彭进松 , 李占宇 . 羰基α-位胺化反应研究进展[J]. 有机化学, 2023 , 43(8) : 2743 -2763 . DOI: 10.6023/cjoc202301005

Abstract

α-Amino carbonyl derivatives are an important class of molecular backbones found in many pharmaceuticals and natural product molecules, meanwhile, they are also an essential kind of intermediates for the synthesis of many organic molecules. To develop simple and efficient method for the synthesis of structurally diversity α-amino carbonyl derivatives of great importance, the amination reactions of carbonyl α-position hydrocarbon bond in recent decades are classified and summarized based on the different activation patterns experienced by the reactions. These reactions are mainly divided into four categories: electrophilic amination, oxidative amination, halide mediated amination, and electrochemical amination.

Key words： α-aminoketone; α-aminoaldehyde; carbonyl compound; electrophilic amination; oxidative amination

参考文献

[1]
Meltzer, P. C.; Butler, D.; Deschamps, J. R.; Madras, B. K. J. Med. Chem. 2006, 49, 1420.
[2]
Carroll, F. I.; Blough, B. E.; Abraham, P.; Mills, A. C.; Holleman, J. A.; Wolckenhauer, S. A.; Decker, A. M.; Landavazo, A.; McElroy, K. T.; Navarro, H. A.; Gatch, M. B.; Forster, M. J. J. Med. Chem. 2009, 52, 6768.
[3]
Silverstone, T. Drugs 1992, 43, 820.
[4]
Marquis, R. W.; Ru, Y.; Yamashita, D. S.; Oh, H. J.; Yen, J.; Thompson, S. K.; Carr, T. J.; Levy, M. A.; Tomaszek, T. A.; Ijames, C. F.; Smith, W. W.; Zhao, B.; Janson, C. A.; Abdel-Meguid, S. S.; DAlessio, K. J.; McQueney, M. S.; Veber, D. F. J. Bioorg. Med. Chem. 1999, 7, 581.
[5]
Nchinda, A. T.; Chibale, K.; Redelinghuys, P.; Sturrock, E. D. Bioorg. Med. Chem. Lett. 2006, 16, 4612.
[6]
Knorr, L. J. Eur. J. Org. Chem. 1888, 1888, 357.
[7]
Sorrell, T. N.; Allen, W. E. J. Org. Chem. 1994, 59, 1589.
[8]
Chiba, T.; Sakagami, H.; Murata, M.; Okimoto, M. J. Org. Chem. 1995, 60, 6764.
[9]
Nadkarni, D.; Hallissey, J.; Mojica, C. J. Org. Chem. 2003, 68, 594.
[10]
Williams, R. M.; Hendrix, J. A. J. Chem. Rev. 1992, 92, 889.
[11]
Xu, J.; Green, A. P.; Turner, N. J. Angew. Chem., Int. Ed. 2018, 57, 16760.
[12]
Fisher, L. E.; Muchowski, J. M. Org. Prep. Proced. Int. 1990, 22, 399.
[13]
Allen, L. A. T.; Raclea, R. C.; Natho, P.; Parsons, P. J. Org. Biomol. Chem. 2021, 19, 498.
[14]
Li, J. Z.; Zhang, W. K.; Ge, G. P.; Zheng, H. X.; Wei, W. T. Org. Biomol. Chem. 2021, 19, 7333.
[15]
Greck, C.; Drouillat, B.; Thomassigny, C. Eur. J. Org. Chem. 2004, 2004, 1377.
[16]
Erdik, E. Tetrahedron. 2004, 60, 8747.
[17]
Greck, C.; Bischoff, l.; Ferreira, F.; Pinel, C.; Piveteau, E.; Genet, J. P. J. Synlett. 1993, 475.
[18]
Bulman Page, P. C.; McKenzie, M. J.; Allina, S. M.; Buckle, D. R. J. Tetrahedron 2000, 56, 9683.
[19]
Asano, T.; Moritani, M.; Nakajima, M.; Kotani, S. Tetrahedron 2017, 73, 5975.
[20]
Evans, D. A.; Nelson, S. G. J. Am. Chem. Soc. 1997, 119, 6452.
[21]
Juhl, K.; J?rgensen, K. A. J. Am. Chem. Soc. 2002, 124, 2420.
[22]
Marigo, M.; Juhl, K.; J?rgensen, K. A. J. Angew. Chem. 2003, 115, 12.
[23]
Ma, S.; Jiao, N.; Zheng, Z.; Ma, Z.; Lu, Z. Org. Lett. 2004, 6, 2193.
[24]
Xiao, X.; Lin, L.; Lian, X.; Liu, X.; Feng, X. Org. Chem. Front. 2016, 3, 809.
[25]
Comelles, J.; Pericas, A.; Moreno-Manas, M.; Vallribera, A.; Drudis-Sole, G.; Lledos, A.; Parella, T.; Roglans, A.; Garcia-Granda, S.; Roces-Fernandez, L. J. Org. Chem. 2007, 72, 2077.
[26]
Pericas, A.; Jimenez, R.; Granados, A.; Shafir, A.; Vallribera, A.; Roglans, A.; Molins, E. ChemistrySelect 2016, 1, 4305.
[27]
Naganawa, Y.; Komatsu, H.; Nishiyama, H. Chem. Lett. 2015, 44, 1652.
[28]
B?gevig, A.; Juhl, K.; Kumaragurubaran, N.; Zhuang, W.; J?rgensen, K. A. J. Angew. Chem., Int. Ed. 2002, 41, 10.
[29]
Kumaragurubaran, N.; Juhl, K.; Zhuang, W.; B?gevig, A.; J?rgensen, K. A. J. J. Am. Chem. Soc. 2002, 124, 6254.
[30]
Iwamura, H.; Wells, D. H.; Mathew, S. P.; Klussmann, M.; Armstrong, A.; Blackmond, D. G. J. J. Am. Chem. Soc. 2004, 126, 16312.
[31]
Franzen, J.; Marigo, M.; Fielenbach, D.; Wabnitz, T. C.; Kj?r- sgaard, A.; J?rgensen, K. A. J. J. Am. Chem. Soc. 2005, 127, 18296.
[32]
Suri, J. T.; Steiner, D. D.; Barbas, C. F. Org. Lett. 2005, 7, 3885.
[33]
Desmarchelier, A.; Yalgin, H.; Coeffard, V.; Moreau, X.; Greck, C. Tetrahedron Lett. 2011, 52, 4430.
[34]
Liu, C.; Zhu, Q.; Huang, K.; Lu, Y. Org. Lett. 2011, 13, 2638.
[35]
Zhou, F.; Zeng, X.; Wang, C.; Zhao, X.; Zhou, J. Chem. Commun. 2013, 49, 2022.
[36]
Lim, Y. J.; Kim, D. Y. B. Bull. Korean. Chem. Soc. 2013, 34, 1955.
[37]
Xu, C.; Zhang, L.; Luo, S. J. Org. Chem. 2014, 79, 11517.
[38]
List, B.; Shevchenko, G.; Pupo, G. Synlett 2015, 26, 1413.
[39]
Odagi, M.; Yamamoto, Y.; Nagasawa, K. Beilstein J. Org. Chem. 2016, 12, 198.
[40]
Shang, M.; Wang, X.; Koo, S. M.; Youn, J.; Chan, J. Z.; Yao, W.; Hastings, B. T.; Wasa, M. J. Am. Chem. Soc. 2017, 139, 95.
[41]
Morisawa, T.; Sawamura, M.; Shimizu, Y. Org. Lett. 2019, 21, 7466.
[42]
Morrill, L. C.; Lebl, T.; Slawina, A. M. Z.; Smith, A. D. Chem. Sci. 2012, 3, 2088.
[43]
Zhang, T.; Cheng, L.; Liu, L.; Wang, D.; Chen, Y. J. Tetrahedron: Asymmetry 2010, 21, 2800.
[44]
Companyo, X.; Valero, G.; Pineda, O.; Calvet, T.; Font-Bardia, M.; Moyano, A.; Rios, R. Org. Biomol. Chem. 2012, 10, 431.
[45]
Jia, L. N.; Huang, J.; Peng, L.; Wang, L. L.; Bai, J. F.; Tian, F.; He, G. Y.; Xu, X. Y.; Wang, L. X. Org. Biomol. Chem. 2012, 10, 236.
[46]
Ohmatsu, K.; Ando, Y.; Nakashima, T.; Ooi, T. Chem 2016, 1, 802.
[47]
Shen, K.; Liu, X.; Wang, G.; Lin, L.; Feng, X. Angew. Chem., Int. Ed. 2011, 50, 4684.
[48]
Sandoval, D.; Frazier, C. P.; Bugarin, A.; Read de Alaniz, J. J. Am. Chem. Soc. 2012, 134, 18948.
[49]
Murru, S.; Lott, C. S.; Fronczek, F. R.; Srivastava, R. S. Org. Lett. 2015, 17, 2122.
[50]
Moriarty, R. M.; Vaid, R. K.; Ravikumar, V. T.; Vaid, B. K.; Hopkins, T. E. J. Tetrahedron 1988, 6, 1603.
[51]
Lee, J. C.; Kim, S.; Shin, W. C. Synth. Commun. 2000, 30, 4271.
[52]
Sun, Y.; Fan, R. Chem. Commun. 2010, 46, 6834.
[53]
Kamble, D. A.; Karabal, P. U.; Chouthaiwale, P. V.; Sudalai, A. Tetrahedron Lett. 2012, 53, 4195.
[54]
Gao, W. C.; Jiang, S.; Wang, R. L.; Zhang, C. Chem. Commun. 2013, 49, 4890.
[55]
Jiang, Q.; Xu, B.; Zhao, A.; Jia, J.; Liu, T.; Guo, C. J. Org. Chem. 2014, 79, 8750.
[56]
Lv, Y.; Li, Y.; Xiong, T.; Lu, Y.; Liu, Q.; Zhang, Q. Chem. Commun. 2014, 50, 2367.
[57]
Wang, D.; Lu, X.; Sun, S.; Yu, H.; Su, H.; Wu, Y.; Zhong, F. Eur. J. Org. Chem. 2019, 2019, 6028.
[58]
Zhong, F.; Chen, G.; Lu, Y. Org. Lett. 2022, 24, 842.
[59]
Takeda, M.; Maejima, S.; Yamaguchi, E.; Itoh, A. Tetrahedron Lett. 2021, 77, 153251.
[60]
Li, K.; Li, Q.; Shi, Q.; He, Y.; Yu, W.; Chang, J. Asian J. Org. Chem. 2022, 11, e202200268.
[61]
Yakura, T.; Yoshimoto, Y.; Ishida, C. J. Chem. Pharm. Bull. 2007, 55, 1385.
[62]
Ton, T. M.; Himawan, F.; Chang, J. W.; Chan, P. W. Chemistry 2012, 18, 12020.
[63]
Tokumasu, K.; Yazaki, R.; Ohshima, T. J. Am. Chem. Soc. 2016, 138, 2664.
[64]
Evans, R. W.; Zbieg, J. R.; Zhu, S.; Li, W.; MacMillan, D. W. J. Am. Chem. Soc. 2013, 135, 16074.
[65]
McDonald, S. L.; Wang, Q. Chem. Commun. 2014, 50, 2535.
[66]
Jia, W. G.; Li, D. D.; Dai, Y. C.; Zhang, H.; Yan, L. Q.; Sheng, E. H.; Wei, Y.; Mu, X. L.; Huang, K. W. Org. Biomol. Chem. 2014, 12, 5509.
[67]
Tran, T. V.; Le, H. T. N.; Ha, H. Q.; Duong, X. N. T.; Nguyen, L. H. T.; Doan, T. L. H.; Nguyen, H. L.; Truong, T. Catal. Sci. Technol. 2017, 7, 3453.
[68]
Rossi, L. I.; Krapacher, C. R.; Granados, A. M. Mol. Catal. 2020, 493, 111058.
[69]
Yu, J.; Liu, S. S.; Cui, J.; Hou, X. S.; Zhang, C. J. Org. Lett. 2012, 3, 832.
[70]
Deng, Q. H.; Bleith, T.; Wadepohl, H.; Gade, L. H. J. Am. Chem. Soc. 2013, 135, 5356.
[71]
Mudaliar, S. S.; Patel, A. P.; Patel, J. J.; Chikhalia, K. H. Tetrahedron Lett. 2018, 59, 734.
[72]
Lu, H.; Lang, K.; Jiang, H.; Wojtas, L.; Zhang, X. P. Chem. Sci. 2016, 7, 6934.
[73]
(a) Kaiser, D.; Maulide, N. J. Org. Chem. 2016, 81, 4421.
[73]
(b) Tona, V.; de la Torre, A.; Padmanaban, M.; Ruider, S.; Gonzalez, L.; Maulide, N. J. Am. Chem. Soc. 2016, 138, 8348.
[74]
Rezayee, N. M.; Rusbjerg, M.; Marx, M.; Linde, S. T.; J?rgensen, K. A. J. Org. Chem. 2022, 87, 1756.
[75]
Wei, Y.; Lin, S.; Liang, F. Org. Lett. 2012, 14, 4202.
[76]
Kumar, Y.; Jaiswal, Y.; Thakur, R.; Kumar, A. ChemistrySelect 2018, 3, 5614.
[77]
Lamani, M.; Prabhu, K. R. Chemistry 2012, 18, 14638.
[78]
Liang, S.; Zeng, C. C.; Tian, H. Y.; Sun, B. G.; Luo, X. G.; Ren, F. Z. J. Org. Chem. 2016, 81, 11565.
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