Synthesis of Chiral Imidazolinone-Based Ionic Liquids

Chin. J. Org. Chem. ›› 2011, Vol. 31 ›› Issue (9): 1433-1439. Previous Articles Next Articles

Full Papers

手性咪唑啉酮离子液体的合成

张焕，李海岗，吴海虹*

(华东师范大学化学系上海市绿色化学与化工工程绿色化重点实验上海 200062)

收稿日期:2010-09-26 修回日期:2011-03-20 发布日期:2011-04-20
通讯作者: 吴海虹 E-mail:hhwu@chem.ecnu.edu.cn

Synthesis of Chiral Imidazolinone-Based Ionic Liquids

ZHANG Huan, LI Hai-Gang, WU Hai-Hong

(Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Department of Chemistry, East China Normal University, Shanghai 200062)

Received:2010-09-26 Revised:2011-03-20 Published:2011-04-20

The chiral ionic liquids have broad applications as inducers for asymmetric reactions. Chiral imidazo1idinones are important sorts of aminocatalysts, which have been attracted much attention in re-search of enantioselective organocatalysis field. From the view of greening and economization, 7 new chiral imidazo1idinone ionic liquids with different anions are synthesized from L-tyrosine, which is a kind of natural chiral materials, through esterfication, amination, cyclization, [3＋2] cycloaddition, etc. The structures and properities were characterized by ¹H NMR, ¹³C NMR, ESI-MS, IR, , DSC and TGA methods.

Key words: L-tyrosine, chiral imidazolidinone, click reaction, chiral ionic liquid

CLC Number:

O621.3

Cite this article

ZHANG Huan, LI Hai-Gang, WU Hai-Hong. Synthesis of Chiral Imidazolinone-Based Ionic Liquids[J]. Chin. J. Org. Chem., 2011, 31(9): 1433-1439.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

References

1. (a) Lee , S.-G, Park, J. H.; Kang J.; Lee, J. K. Chem. Commun. 2001, 1698

(b) Yadav, J. S.; Reddy, B. V. S.; Baishya, G. J. Org. Chem. 2003, 68, 7098

2. Liu, W.-S.; Tao, G.-H.; He, L.; Kou, Y.; Chin. J. Org. Chem. 2006, 26, 1031(in chinese)

(刘伟山; 陶国宏; 何玲; 寇元有机化学，2006，26，1031)

3. (a) Wasserscheid, P.; B?smanna, A.; Bolmb C. Chem. Commun. 2002, 200

(b) Luo, S.-Z.; Mi, X.-L. ; Zhang, L.; Liu, S.; Xu, H.; Cheng, J.-P. Tetrahedron 2007, 63, 1923.

(c) Cao, X.; Yue, C.-G.; Chin. J. Org. Chem. 2010, 30, 816 (in chinese)

(曹霞; 乐长高有机化学，2010，30，816)

4. Howarth, J.; HanIon, K.; Fayne, D.; McCormac, P. Tetrahed. Lett . 1997, 38, 3097

5. Wu, N.; Wu, H.-H.; Jiang, Y.-W.; Chin. J. Org. Chem. 2008, 28, 104 (in chinese)

(吴楠; 吴海虹; 蒋咏文有机化学，2008，28，104)

6. Siyutkin, D. E.; Kucherenko, A. S.; Struchkova, M. I.; Zlotin, S. G. Tetrahedron Lett. 2008, 49, 1212.

7. Li, F. -R.; Song, Q.; Zhao, L.; Yuan, L.-M.; Chem. J. Chin. Universities, 2009, 30, 258 (in chinese)

(李芙蓉; 宋卿; 赵丽; 袁黎明高等学校化学学报, 2009, 30, 258)

8. (a) Loh, T. P.; Feng, L. C.; Yang, H. Y.; Yang, J. Y. Tetrahedron Lett. 2002 43, 8741

(b) Luo, S.-P.; Wang, L.-P.; Yue, H.-D.; Yue, C.-G.; Yang, W.-L.; Xu, D.-Q.; Xu. Z.-Y.; Acta Chimica Sinica, 2006, 64, 1483 (in chinese)

(罗书平; 王丽萍; 岳华栋; 乐长高; 杨文龙; 许丹倩; 徐振元化学学报, 2006, 64, 1483)

9. Austin, J. F. ; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 1172.

10. Yao, C.-F.; Sun, C.-X.; Yan, S.-Y.; Wu, H.-H.; Progress in Chem. 2008, 20(6), 887 (in chinese).

(姚成福; 孙彩霞; 闫少宇; 吴海虹化学进展, 2008, 20, 887)

11. Northrup, A. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 2458.

12. Jen, W. S.; Wiener, J. J. M.; MacMillan, D. W. C. J. Am. Chem. Soc. 2000 , 122,

9874

13. (a) Brown, S. P.; Goodwin, N. C.; MacMillan, D. W. C. J. Am. Chem. Soc. 2003, 125, 1192.

(b) Fonseca, M. T. H.; List, B. Angew. Chem. Int. Ed. 2004 , 43, 3958.

14. (a) Brochu, M. P.; Brown, S. P.; MacMillan, D. W. C. J. Am. Chem. Soc. 2004, 126, 4108.

(b) Beeson, T. D.; MacMillan, D. W. C. J. Am. Chem. Soc., 2005, 127, 8826.

15. Paras, N. A.; MaeMillan, D. W. C. J. Am. Chem. Soc., 2001,123,4370

16. Yao, L.; Smith, B. T.; Aube, J. J. Org. Chem. 2004, 69, 1720.

17. Nonaka, H.; Tsukiji, S.; Ojida, A.; Hamachi, I.; J. Am. Chem. Soc. 2007, 129, 15777.

18. Ciampi, S.; Bocking, T.; Kilian, K. A.; James, M.; Harper, J. B.; Gooding, J. J. Langmuir 2007, 23, 9320.

[1]	Wu, Jiacheng, Liu, Zhenghui, Yao, Yuan, Lin, Shaoliang. Synthesis and Self-Assembly of Alternating Amphiphilic Copolymer with Azobenzene Pendants [J]. Chinese Journal of Organic Chemistry, 2019, 39(10): 2952-2957.
[2]	Zhao Bangtun, Tao Jingjing, Chen Xiaoji, Zhu Weimin. Progress on Synthesis and Application of Triazole-Based Tetrathiafulvalene Derivatives [J]. Chin. J. Org. Chem., 2017, 37(8): 1964-1977.
[3]	Pan Guojun, Xiao Na, Shen Di, Chen Minglang, Li Yi, Lu Kui, Yang Yang, Meng Xin, Yu Peng. Synthesis and Hypoglycemic Activity of Novel Quercetin Conjugates [J]. Chin. J. Org. Chem., 2017, 37(1): 133-140.
[4]	Shen Baoxing, Qian Ying. A Novel Fluorescent Dye Naphthalene Imide-Fluorine Boron Two Pyrrole: Synthesis, Fluorescence Resonance Energy Transfer and Cell Imaging [J]. Chin. J. Org. Chem., 2016, 36(4): 774-781.
[5]	Huo Jingpei, Wei Xinping, Mo Guangzhen, Peng Pai, Zhong Mingli, Chen Renhong, Wang Zhaoyang. Progresses in Syntheses and Applications of Bis-1,2,3-triazoles [J]. Chin. J. Org. Chem., 2014, 34(1): 92-106.
[6]	XIONG Xin-Quan. One-Pot Synthesis of Dendrimers via double click reactions [J]. Chin. J. Org. Chem., 2010, 30(02): 307-310.

手性咪唑啉酮离子液体的合成

Synthesis of Chiral Imidazolinone-Based Ionic Liquids

PDF

Knowledge

Cited

Abstract

Cite this article

share this article

References

Related Articles 6

Recommended Articles

Metrics

Comments