Synthesis of a New Class of Chiral Maleimide Derivatives with C2-Symmetry

doi:10.6023/cjoc201703001

Chin. J. Org. Chem. ›› 2017, Vol. 37 ›› Issue (10): 2685-2689.DOI: 10.6023/cjoc201703001 Previous Articles Next Articles

ARTICLE

一类具有C₂对称性的轴手性马来酰亚胺类化合物的合成

符立言^a,b, 吉保明^a, 杜晨霞^b

a 洛阳师范学院化学化工学院洛阳 471022;
b 郑州大学化学与分子工程学院郑州 450001

收稿日期:2017-03-01 修回日期:2017-06-07 发布日期:2017-06-23
通讯作者: 吉保明 E-mail:lyhxxjbm@126.com
基金资助:
国家自然科学基金（No.21372112）资助项目.

Synthesis of a New Class of Chiral Maleimide Derivatives with C₂-Symmetry

Fu Liyan^a,b, Ji Baoming^a, Du Chenxia^b

a College of Chemistry and Chemical Engineering, Luoyang Normal University, Luoyang 471022;
b College of Chemistry and Molecular Engineering, Zhengzhou University, Zhengzhou 450001

Received:2017-03-01 Revised:2017-06-07 Published:2017-06-23
Contact: 10.6023/cjoc201703001 E-mail:lyhxxjbm@126.com
Supported by:
Project supported by the National Natural Science Foundation of China (No.21372112).

1. Synthesis of a New Class of Chiral Maleimide Derivatives with C₂-Symmetry.PDF(1434KB)

Abstract

Starting from the readily available maleic anhydride and (R)-1,1'-bi-2-naphthol (BINOL), an efficient method for the synthesis of a new class of chiral maleimide derivatives with C₂-symmetry was described, involving Williamson ether synthesis, Suzuki coupling reaction and deprotection reaction by microwave to give 3,4-[(R)-3,3'-diaryl-1,1'-binaphthyl-2,2'-dioxy]-maleimides in 6.2%~16% yields. Moreover, the structures of the target compound and key intermediates were confirmed by ¹H NMR, ¹³C NMR, HRMS and IR techniques.

Key words: imide, BINOL, organic synthesis, chirality

Cite this article

Fu Liyan, Ji Baoming, Du Chenxia. Synthesis of a New Class of Chiral Maleimide Derivatives with C₂-Symmetry[J]. Chin. J. Org. Chem., 2017, 37(10): 2685-2689.

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[1] Hu, Y.-F. In Modern Organic Synthesis Reagents, Vol. 4, Chemical Industry Press, Beijing, 2011, p. 97(in Chinese). (胡跃飞, 现代有机合成试剂, 第四卷, 化学工业出版社, 北京, 2011, p. 97.)
[2] Pu, L. Chem. Rev. 1998, 98, 2405.
[3] Gao, Y.-J.; Yang, L.-H.; Song, S.-J.; Ma, J.-J.; Tang, R.-X.; Bian, R.-H.; Liu, H.-Y.; Wu, Q.-H.; Wang, C. Chin. J. Org. Chem. 2008, 28, 8(in Chinese). (高勇军, 杨丽华, 宋双居, 马晶军, 唐然肖, 边瑞环, 刘海燕, 吴秋华, 王春, 有机化学, 2008, 28, 8.)
[4] Chen, Y. Y.; Jiang, Y. J.; Fan, Y. S.; Sha, D.; Wang, Q. F.; Zhang, G.; Zheng, L.; Zhang, S. Tetrahedron:Asymmetry 2012, 23, 904.
[5] Xu, S.; Wang, Z.; Zhang, X.; Ding, K. Eur. J. Org. Chem. 2011, 110.
[6] Xu, S.; Wang, Z.; Li, Y.; Zhang, X.; Wang, H.; Ding, K. Chem.-Eur. J. 2010, 16, 3021.
[7] Sengoku, T.; Murata, Y.; Aso. Y.; Kawakami, A.; Inuzuka, T.; Sakamoto, M.; Takahashi, M.; Yoda, H. Org. Lett. 2015, 17, 5846.
[8] Marminon, C.; Pierre, A.; Pfeiffer, B.; Perez, V.; Leonce, S.; Renard, P.; Prudhomme, M. Bioorg. Med. Chem. 2003, 11, 679.
[9] Wang, K.; Yan, Z.; Wang, N.; Liu, Z. Z. Chin. Chem. Lett. 2012, 23, 462.
[10] Rigby, J. H.; Mateo, M. E. J. Am. Chem. Soc. 1997, 119, 12655.
[11] Rigby, J. H.; Maharoof, U. S. M.; Meteo, M. E. J. Am. Chem. Soc. 2000, 122, 6624.
[12] Awuah, E.; Capretta, A. J. Org. Chem. 2011, 76, 3122.
[13] Chung, J. Y. L.; Cai, C.; McMilliams, J. C.; Reamer, B. A.; Peter, G. D.; Cvetovich, R. J. J. Org. Chem. 2005, 70, 10342.
[14] Bartlett, S.; Nelson, A.; Org. Biomol. Chem. 2004, 2, 2874.
[15] Shen, L.; Prouty, C.; Conway, B. R.; Westover, L.; Xu, J. Z.; Look, R. A.; Chen, X.; Beavers, M. P.; Roberts, J.; Murray, W. V.; Demarest, K. T.; Kuo, H. Bioorg. Med. Chem. 2004, 12, 1239.
[16] Brenet, S.; Berthiol, F.; Einhorn, J. Eur. J. Org. Chem. 2013, 8094.
[17] Paik, S.; Lee, J. Y. Tetrahedron Lett. 2006, 47, 1813.
[18] Brenet, S.; Baptiste, B.; Philouze, C.; Berthiol, F.; Einhorn, J. Eur. J. Org. Chem. 2013, 1041.
[19] Dubernet, M.; Caubert, V.; Guillard, J.; Claude, M.; Massuard, V. Tetrahedron. 2005, 61, 4585.
[20] Wuts. P. G. M.; Greene, T. W. Greene's Protective Groups in Organic Synthesis, John Wiley & Sons, New Jersey, 2007, p. 905.
[21] Akiyama, T.; Takesue, Y.; Kumegawa, M.; Nishimoto, H.; Ozaki, S. Bull. Chem. Soc. Jpn. 1991, 64, 2266.
[22] Banwell, M. G.; Hamel, E.; Hockless, D. C. R.; Verdier-Pinard, P.; Willis, A. C.; Wong, D. J. Bioorg. Med. Chem. 2006, 14, 4627.
[23] Subramanyam, C. Synth. Commun. 1995, 25, 761.
[24] Zhou, X.; Liu, W. J.; Ye, J. L.; Huang, P. Q. Tetrahedron 2007, 63, 6346.
[25] Williams, R. M.; Glinka, T.; Kwast. E.; Coffman, H.; Stille, J. K. J. Am. Chem. Soc. 1990, 112, 808.
[26] Kumar, M.; Kukhsana, I. K.; Saravanan, S.; Verma, S.; Jakhar, A.; Khan, N. H.; Abdi, S. H.; Bajaj, H. C. Org. Lett. 2014, 16, 2798.
[27] Roy, S.; Bhanja, P.; Islam, S. S.; Bhaumik, A.; Islam, S. M. Chem. Commun. 2016, 52, 1871.
[28] Goldys, A.; McErlean, C. S. P. Tetrahedron Lett. 2009, 50, 3985.

一类具有C₂对称性的轴手性马来酰亚胺类化合物的合成

Synthesis of a New Class of Chiral Maleimide Derivatives with C₂-Symmetry

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一类具有C2对称性的轴手性马来酰亚胺类化合物的合成