Citation: Mao Pu, Yang Liangru, Xiao Yongmei, Yuan Jinwei, Mai Wenpeng, Gao Jie, Zhang Xinchi. Synthesis of Chiral Imidazole Amino Alcohols and Their Application in the Asymmetric Copper-Catalyzed Henry Reaction[J]. Chinese Journal of Organic Chemistry, ;2019, 39(2): 443-448. doi: 10.6023/cjoc201807008 shu

Synthesis of Chiral Imidazole Amino Alcohols and Their Application in the Asymmetric Copper-Catalyzed Henry Reaction

Mao Pu ^a,, ,
Yang Liangru ^a,, ,
Xiao Yongmei ^a ,
Yuan Jinwei ^a ,
Mai Wenpeng ^b ,
Gao Jie ^a ,
Zhang Xinchi ^a

a.
Academician Workstation for Natural Medicinal Chemistry of Henan Province, School of Chemical Engineering and Environment, Henan University of Technology, Zhengzhou 450001
b.
School of Material and Chemical Engineering, Henan University of Engineering, Zhengzhou 451191

Corresponding author: Mao Pu, maopu@haut.edu.cn Yang Liangru, lryang@haut.edu.cn
Received Date: 4 July 2018
Revised Date: 31 August 2018
Available Online: 26 February 2018
Fund Project: the Program for Innovative Research Team from Zhengzhou City 131PCXTD605the National Natural Science Foundation of China 21172055the Fundamental Research Funds for the Henan Provincial Colleges and Universities in Henan University of Technology 2017RCJH08Project supported by the National Natural Science Foundation of China (No. 21172055), the Natural Science Foundation of Henan Province Department of Education (No. 18A150004), the Program for Innovative Research Team from Zhengzhou City (No. 131PCXTD605), and the Fundamental Research Funds for the Henan Provincial Colleges and Universities in Henan University of Technology (No. 2017RCJH08)the Natural Science Foundation of Henan Province Department of Education 18A150004

Figures(3)

Using L-phenylalaninol as chiral precursor, a series of multi-aryl substituted imidazole amino alcohol derivatives containing appended chiral functionalities were synthesized through a "four component-one pot procedure" from the condensation reaction of L-phenylalaninol, dibenzoyl (benzil), ammonium acetate and different heterocyclic aryl-aldehyde. X-ray crystal analysis confirmed that the chiral carbon retained the S configuration of L-phenylalaninol. The chiral ligands in combination with Cu(OAc)₂·H₂O catalyzed the enantioselective Henry reaction of nitromethane and aromatic aldehydes with moderate to high yields and excellent enantioselectivities (>99%) with S configuration. The easy availability of catalyst components, mild reaction conditions and high enantioselectivity make the system attractive for practical application.
- chiral,
- imidazole amino alcohol,
- asymmetric Henry reaction
1. [1]
  Rosini, G. In Comprehensive Organic Synthesis, Vol. 2, Eds.: Trost, B. M., Fleming, I., Pergamon, Oxford, UK, 1999, p. 321.
2. [2]
  Pinnick, H. W. In Organic Reactions, Vol. 38, Ed.: Paquette, L. A., Wiley, New York, 1990, Chapter 3.
3. [3]
  Palomo, C.; Oiarbide, M.; Laso, A. Eur. J. Org. Chem. 2007, 2561.
4. [4]
  Ono, N. The Nitro Group in Organic Synthesis, Wiley-VCH, New York, 2001.
5. [5]
  Shibasaki, M.; Gröger, H. In Comprehensive Asymmetric Catalysis, Vol. Ⅲ, Eds.:Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H.; Springer, Berlin, Germany, 1999, p. 1075.
6. [6]
  Shibasaki, M.; Gröger, H.; Kanai, M. In Comprehensive Asymmetric Catalysis, Eds.: Supplement, I.; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Springer, Heidelberg, Germany, 2004, p. 131.
7. [7]
  Luzzio, F. A. Tetrahedron 2001, 57, 915. doi: 10.1016/S0040-4020(00)00965-0
8. [8]
  Bandini, M.; Piccinelli, F.; Tommasi, S.; Ronchi, A. U.; Ventrici, C. Chem. Commun. 2007, 616.
9. [9]
  Blay, G.; Hernández-Olmos, V.; Pedro, J. R. Synlett 2011, 1195.
10. [10]
  Palomo, C.; Oiarbide, M.; Mielgo, A. Angew. Chem., Int. Ed. 2004, 43, 5442. doi: 10.1002/(ISSN)1521-3773
11. [11]
  Zhang, S.; Li, Y.; Xu, Y.; Wang, Z. Chin. Chem. Lett. 2018, 29, 873. doi: 10.1016/j.cclet.2017.10.001
12. [12]
  Bhatt, A. P.; Pathak, K.; Jasra, R. V.; Kureshy, R. I.; Khan, N. H.; Abdi, S. H. R. J. Mol. Catal. A:Chem. 2006, 244, 110. doi: 10.1016/j.molcata.2005.08.045
13. [13]
  Trost, B. M.; Yeh, V. S. C. Angew. Chem., Int. Ed. 2002, 41, 861. doi: 10.1002/1521-3773(20020301)41:5<861::AID-ANIE861>3.0.CO;2-V
14. [14]
  Palomo, C.; Oiarbide, M.; Laso, A. Angew. Chem., Int. Ed. 2005, 44, 3881. doi: 10.1002/(ISSN)1521-3773
15. [15]
  Liu, S. L.; Wolf, C. Org. Lett. 2008, 10, 1831. doi: 10.1021/ol800442s
16. [16]
  Bulut, A.; Aslan, A.; Dogan, Ö. J. Org. Chem. 2008, 73, 7373.
17. [17]
  Park, J.; Lang, K.; Abboud, K. A.; Hong, S. J. Am. Chem. Soc. 2008, 130, 16484. doi: 10.1021/ja807221s
18. [18]
  Kogami, Y.; Nakajima, T.; Ikeno, T.; Yamada, T. Synthesis 2004, 1947.
19. [19]
  Kowalczyk, R.; Kwiatkowski, P.; Skarzewski, J.; Jurczak, J. J. Org. Chem. 2009, 74, 753. doi: 10.1021/jo802107b
20. [20]
  Zulauf, A.; Mellah, M.; Schulz, E. J. Org. Chem. 2009, 74, 2242. doi: 10.1021/jo802769y
21. [21]
  Choudary, B. M.; Ranganath, K. V. S.; Pal, U.; Kantam, M. L.; Sreedhar, B. J. Am. Chem. Soc. 2005, 127, 13167. doi: 10.1021/ja0440248
22. [22]
  Sasai, H.; Suzuki, T.; Arai, S.; Arai, T.; Shibasaki, M. J. Am. Chem. Soc. 1992, 114, 4418. doi: 10.1021/ja00037a068
23. [23]
  Christensen, C.; Juhl, K.; Hazell, R. G.; Jørgensen, K. A. J. Org. Chem. 2002, 67, 4875. doi: 10.1021/jo025690z
24. [24]
  Xiong, Y.; Wang, F.; Huang, X.; Wen, Y.; Feng, X. Chem.-Eur. J. 2007, 13, 829. doi: 10.1002/(ISSN)1521-3765
25. [25]
  Bandini, M.; Piccinelli, F.; Tommasi, S.; Umani-Ronchi, A.; Ventrici, C. Chem. Commun. 2007, 616.
26. [26]
  Arai, T.; Takashita, R.; Endo, Y.; Watanabe, M.; Yanagisawa, A. J. Org. Chem. 2008, 73, 4903. doi: 10.1021/jo800412x
27. [27]
  Ma, K.; You, J. Chem.-Eur. J. 2007, 13, 1863. doi: 10.1002/(ISSN)1521-3765
28. [28]
  Dixit, A.; Kumar, P.; Yadav, G. D.; Singh, S. Inorg. Chim. Acta 2018, 479, 240. doi: 10.1016/j.ica.2018.04.048
29. [29]
  Khlebnikova, T. B.; Konev, V. N.; Pai, Z. P. Tetrahedron 2018, 74, 260. doi: 10.1016/j.tet.2017.11.059
30. [30]
  Christensen, C.; Juhl, K.; Jørgensen, K. A. Chem. Commun. 2001, 2222.
31. [31]
  Evans, D. A.; Seidel, D.; Rueping, M.; Lam, H. W.; Shaw, J. T.; Downey, C. W. J. Am. Chem. Soc. 2003, 125, 12692. doi: 10.1021/ja0373871
32. [32]
  McManus, H. A.; Guiry, P. J. Chem. Rev. 2004, 104, 4151. doi: 10.1021/cr040642v
33. [33]
  Desimoni, G.; Faita, G.; Jørgensen, K. A. Chem. Rev. 2006, 106, 3561. doi: 10.1021/cr0505324
34. [34]
  Hargaden, G. C.; Guiry, P. J. Chem. Rev. 2009, 109, 2505. doi: 10.1021/cr800400z
35. [35]
  Aydin, A. E.; Yuksekdanaci, S. Tetrahedron:Asymmetry 2013, 24, 14. doi: 10.1016/j.tetasy.2012.11.022
36. [36]
  Wolinska, E. Tetrahedron:Asymmetry 2014, 25, 1122. doi: 10.1016/j.tetasy.2014.06.019
37. [37]
  Cruz, H.; Aguirre, G.; Madrigal, D. Chavez, D.; Somanathan, R. Tetrahedron:Asymmetry 2016, 27, 1217. doi: 10.1016/j.tetasy.2016.10.007
38. [38]
  Liu, S.; Wolf, C. Org. Lett. 2008, 10, 1831. doi: 10.1021/ol800442s
39. [39]
  Spangler, K. Y.; Wolf, C. Org. Lett. 2009, 11, 4724. doi: 10.1021/ol9018612
40. [40]
  Toussaint, A.; Pfaltz, A. Eur. J. Org. Chem. 2008, 14, 459. doi: 10.1002/(ISSN)1521-3765
41. [41]
  Kowalczyk, R.; Sidorowicz, L.; Skarzewski, J. Tetrahedron:Asymmetry 2008, 19, 2310. doi: 10.1016/j.tetasy.2008.09.032
42. [42]
  Selvakumar, S.; Sivasankaran, D.; Singh, V. K. Org. Biomol. Chem. 2009, 7, 3156. doi: 10.1039/b904254g
43. [43]
  Chunhong, Z.; Liu, F.; Gou, S. Tetrahedron:Asymmetry 2014, 25, 278. doi: 10.1016/j.tetasy.2013.12.017
44. [44]
  Cwiek, R.; Nideziejko, P.; Kaluza, Z. J. Org. Chem. 2014, 79, 1222. doi: 10.1021/jo402631u
45. [45]
  El-Asaad, B.; Metay, E.; Karame, I.; Lemaire, M. Mol. Catal. 2017, 435, 76. doi: 10.1016/j.mcat.2017.03.017
46. [46]
  Jin, W.; Li, X.; Huang, Y.; Wu, F.; Wan, B. Chem.-Eur. J. 2010, 16, 8259. doi: 10.1002/chem.v16:28
47. [47]
  Otevrel, J.; Bobal, P. J. Org. Chem. 2017, 82, 8342. doi: 10.1021/acs.joc.7b00079
48. [48]
  Wu, L.; Su, Y.; Chong, S.; Zhang, W.; Huang, D.; Wang, K.; Hu, Y. Chin. J. Org. Chem. 2017, 37, 936(in Chinese).
49. [49]
  Blay, G.; Climent, E.; Fernández, I.; Hernández-Olmos, V.; Pedro, J. R. Tetrahedron:Asymmetry 2007, 18, 1603. doi: 10.1016/j.tetasy.2007.06.023
50. [50]
  Blay, G.; Hernández-Olmos, V.; Pedro, J. R. Chem. Commun. 2008, 4840.
51. [51]
  Arai, T.; Suzuki, K. Synlett 2009, 3167.
52. [52]
  Sappino, C.; Mari, A.; Mantineo, A.; Moliterno, M.; Palagri, M.; Tatangelo, C.; Suber, L.; Bovicelli, P.; Ricelli, A.; Righi, G. Org. Biomol. Chem. 2018, 16, 1860. doi: 10.1039/C8OB00165K
53. [53]
  Vicario, J.; Badia, D.; Carrillo, L.; Reyes E.; Etxebarria, J. Curr. Org. Chem. 2005, 9, 219. doi: 10.2174/1385272053369105
54. [54]
  Ager, D. J.; Prakash, I.; Schaad, D. R. Chem. Rev. 1996, 96, 835. doi: 10.1021/cr9500038
55. [55]
  Guo, J.; Mao, J. Chirality 2009, 21, 619. doi: 10.1002/chir.v21:6
56. [56]
  Xu, F.; Lei, C.; Yan, L.; Tu, J.; Li, G. Chirality 2015, 27, 761. doi: 10.1002/chir.22498
57. [57]
  Lu, G.; Zheng, F.; Wang, L.; Guo, Y.; Li, X.; Cao, X.; Wang, C.; Chi, H.; Dong, Y.; Zhang, Z. Tetrahedron:Asymmetry 2016, 27, 732. doi: 10.1016/j.tetasy.2016.06.018
58. [58]
  Chen, W.; Zhou, Z., Chen, H. Org. Biomol. Chem. 2017, 15, 1530. doi: 10.1039/C6OB02569B
59. [59]
  Bao, W.; Wang, Z.; Li, Y. J. Org. Chem. 2003, 68, 591. doi: 10.1021/jo020503i
60. [60]
  Mao, P.; Cai, Y.; Xiao, Y.; Yang, L.; Xue, Y.; Song, M. Phosphorus, Sulfur Silicon Relat. Elem. 2010, 185, 2418. doi: 10.1080/10426501003671460
61. [61]
  Matsuoka, Y.; Ishida, Y.; Sasaki, D.; Saigo, K. Tetrahedron 2006, 62, 8199. doi: 10.1016/j.tet.2006.05.079
62. [62]
  Xiao, Y.; Yang, L.; He, K.; Yuan, J.; Mao, P. Acta Crystallogr. 2012, E68, o264.
63. [63]
  Yang, L.; Xiao, Y.; He, K.; Yuan, J.; Mao, P. Acta Crystallogr. 2012, E68, o1670.
64. [64]
  Kodama, K.; Sugawara, K.; Hirose, T. Chem.-Eur. J. 2011, 17, 13584. doi: 10.1002/chem.v17.48
1. [1]
  Ruixue Liu , Xiaobing Ding , Qiwei Lang , Gen-Qiang Chen , Xumu Zhang . Enantioselective and divergent construction of chiral amino alcohols and oxazolidin-2-ones via Ir-f-phamidol-catalyzed dynamic kinetic asymmetric hydrogenation. Chinese Chemical Letters, 2025, 36(3): 110037-. doi: 10.1016/j.cclet.2024.110037
2. [2]
  Zhen Liu , Zhi-Yuan Ren , Chen Yang , Xiangyi Shao , Li Chen , Xin Li . Asymmetric alkenylation reaction of benzoxazinones with diarylethylenes catalyzed by B(C₆F₅)₃/chiral phosphoric acid. Chinese Chemical Letters, 2024, 35(5): 108939-. doi: 10.1016/j.cclet.2023.108939
3. [3]
  Chuan-Zhi Ni , Ruo-Ming Li , Fang-Qi Zhang , Qu-Ao-Wei Li , Yuan-Yuan Zhu , Jie Zeng , Shuang-Xi Gu . A chiral fluorescent probe for molecular recognition of basic amino acids in solutions and cells. Chinese Chemical Letters, 2024, 35(10): 109862-. doi: 10.1016/j.cclet.2024.109862
4. [4]
  Long Jin , Jian Han , Dongmei Fang , Min Wang , Jian Liao . Pd-catalyzed asymmetric carbonyl alkynylation: Synthesis of axial chiral ynones. Chinese Chemical Letters, 2024, 35(6): 109212-. doi: 10.1016/j.cclet.2023.109212
5. [5]
  Xin Li , Jia-Min Lu , Bo Li , Chen Zhao , Bei-Bei Yang , Li Li . Chiroptical sensing for remote chiral amines via a C–H activation reaction. Chinese Chemical Letters, 2025, 36(5): 110310-. doi: 10.1016/j.cclet.2024.110310
6. [6]
  Xinghui Yao , Zhouyu Wang , Da-Gang Yu . Sustainable electrosynthesis: Enantioselective electrochemical Rh(III)/chiral carboxylic acid-catalyzed oxidative CH cyclization coupled with hydrogen evolution reaction. Chinese Chemical Letters, 2024, 35(9): 109916-. doi: 10.1016/j.cclet.2024.109916
7. [7]
  Zhiwen Li , Jingjing Zhang , Gao Li . Dynamic assembly of chiral golden knots. Chinese Journal of Structural Chemistry, 2024, 43(7): 100300-100300. doi: 10.1016/j.cjsc.2024.100300
8. [8]
  Jiayu Xu , Meng Li , Baoxia Dong , Ligang Feng . Fully fluorinated hybrid zeolite imidazole/Prussian blue analogs with combined advantages for efficient oxygen evolution reaction. Chinese Chemical Letters, 2024, 35(6): 108798-. doi: 10.1016/j.cclet.2023.108798
9. [9]
  Xiang Huang , Dongzhen Xu , Yang Liu , Xia Huang , Yangfan Wu , Dongmei Fang , Bing Xia , Wei Jiao , Jian Liao , Min Wang . Asymmetric synthesis of difluorinated α-quaternary amino acids (DFAAs) via Cu-catalyzed difluorobenzylation of aldimine esters. Chinese Chemical Letters, 2024, 35(12): 109665-. doi: 10.1016/j.cclet.2024.109665
10. [10]
  Wenying Cui , Zhetong Jin , Wentao Fu , Chengshuo Shen . Flag-hinge-like highly luminescent chiral nanographenes with twist geometry. Chinese Chemical Letters, 2024, 35(11): 109667-. doi: 10.1016/j.cclet.2024.109667
11. [11]
  Genlin Sun , Yachun Luo , Zhihong Yan , Hongdeng Qiu , Weiyang Tang . Chiral metal-organic frameworks-based materials for chromatographic enantioseparation. Chinese Chemical Letters, 2024, 35(12): 109787-. doi: 10.1016/j.cclet.2024.109787
12. [12]
  Teng-Yu Huang , Junliang Sun , De-Xian Wang , Qi-Qiang Wang . Recent progress in chiral zeolites: Structure, synthesis, characterization and applications. Chinese Chemical Letters, 2024, 35(12): 109758-. doi: 10.1016/j.cclet.2024.109758
13. [13]
  Chuang LIU , Lichao SUN , Qingfeng ZHANG . Chiral inorganic nanocatalysts for electrochemical and enzyme-mimicked biosensing. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 59-78. doi: 10.11862/CJIC.20240406
14. [14]
  Cong Gao , Zijian Zhu , Siwei Li , Zheng Xi , Qingqing Sun , Jie Han , Rong Guo . Chiral supramolecular catalysts of helical nanoribbon: More twist, higher enantioselectivity. Chinese Chemical Letters, 2025, 36(3): 109968-. doi: 10.1016/j.cclet.2024.109968
15. [15]
  Yan-Bo Li , Yi Li , Liang Yin . Copper(Ⅰ)-catalyzed diastereodivergent construction of vicinal P-chiral and C-chiral centers facilitated by dual "soft-soft" interaction. Chinese Chemical Letters, 2024, 35(7): 109294-. doi: 10.1016/j.cclet.2023.109294
16. [16]
  Yu-Hang Miao , Zheng-Xu Zhang , Xu-Yi Huang , Yuan-Zhao Hua , Shi-Kun Jia , Xiao Xiao , Min-Can Wang , Li-Ping Xu , Guang-Jian Mei . Catalytic asymmetric dearomative azo-Diels–Alder reaction of 2-vinlyindoles. Chinese Chemical Letters, 2024, 35(4): 108830-. doi: 10.1016/j.cclet.2023.108830
17. [17]
  Jieshuai Xiao , Yuan Zheng , Yue Zhao , Zhuangzhi Shi , Minyan Wang . Asymmetric Nozaki-Hiyama-Kishi (NHK)-type reaction of isatins with aromatic iodides by cobalt catalysis. Chinese Chemical Letters, 2025, 36(5): 110243-. doi: 10.1016/j.cclet.2024.110243
18. [18]
  Changhui Yu , Peng Shang , Huihui Hu , Yuening Zhang , Xujin Qin , Linyu Han , Caihe Liu , Xiaohan Liu , Minghua Liu , Yuan Guo , Zhen Zhang . Evolution of template-assisted two-dimensional porphyrin chiral grating structure by directed self-assembly using chiral second harmonic generation microscopy. Chinese Chemical Letters, 2024, 35(10): 109805-. doi: 10.1016/j.cclet.2024.109805
19. [19]
  Zhao-Xia Lian , Xue-Zhi Wang , Chuang-Wei Zhou , Jiayu Li , Ming-De Li , Xiao-Ping Zhou , Dan Li . Producing circularly polarized luminescence by radiative energy transfer from achiral metal-organic cage to chiral organic molecules. Chinese Chemical Letters, 2024, 35(8): 109063-. doi: 10.1016/j.cclet.2023.109063
20. [20]
  Yongjing Deng , Feiyang Li , Zijian Zhou , Mengzhu Wang , Yongkang Zhu , Jianwei Zhao , Shujuan Liu , Qiang Zhao . Chiral induction and Sb³⁺ doping in indium halides to trigger second harmonic generation and circularly polarized luminescence. Chinese Chemical Letters, 2024, 35(8): 109085-. doi: 10.1016/j.cclet.2023.109085

Get Citation

PDF

XML

Metrics

PDF Downloads(48)
Abstract views(704)
HTML views(81)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142