Application of N-Oxides as Organocatalysts in Asymmetric Reaction

doi:10.6023/cjoc201411020

Chin. J. Org. Chem. ›› 2015, Vol. 35 ›› Issue (5): 975-983.DOI: 10.6023/cjoc201411020 Previous Articles Next Articles

REVIEW

氮氧化物有机小分子催化剂在不对称反应中的应用

白冰, 杨静, 张改红, 毛多斌

郑州轻工业学院食品与生物工程学院郑州 450000

收稿日期:2014-11-11 修回日期:2014-12-10 发布日期:2015-01-05
通讯作者: 白冰 E-mail:baibing82@163.com
基金资助:
郑州轻工业学院博士基金(No.2013BSJJ009)资助项目.

Application of N-Oxides as Organocatalysts in Asymmetric Reaction

Bai Bing, Yang Jing, Zhang Gaihong, Mao Duobin

School of Food & Biological Engineering, Zhengzhou University of Light Industry, Zhengzhou 450000

Received:2014-11-11 Revised:2014-12-10 Published:2015-01-05
Supported by:
Project supported by the Doctoral Fund Project of Zhengzhou University of Light Industry (No.2013BSJJ009).

Cite this article

Bai Bing, Yang Jing, Zhang Gaihong, Mao Duobin. Application of N-Oxides as Organocatalysts in Asymmetric Reaction[J]. Chin. J. Org. Chem., 2015, 35(5): 975-983.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Chen, J.; Liu, Q.; Dai, X.-Y.; Nie, L.-L.; Fang, H.-H, Wu, X.-Y. Chin. J. Org. Chem. 2013, 33, 1 (in Chinese). (陈杰, 刘钦, 戴小鸯, 聂凛凛, 房辉辉, 吴小余, 有机化学, 2013, 33, 1.)
[2] Hou, X.-H.; Ma, Z.-W.; Wang, J.-L.; Liu, H.-M. Chin. J. Org. Chem. 2014, 34, 1509 (in Chinese). (侯学会, 马志伟, 王建玲, 刘宏民, 有机化学, 2014, 34, 1509.)
[3] Nakajima, M.; Saito, M.; Shiro, M.; Hashimoto, S. J. Am. Chem. Soc. 1998, 120, 6419.
[4] Liu, X. H.; Lin, L. L.; Feng, X. M. Acc. Chem. Res. 2011, 44, 574.
[5] Xie, M.-S.; Wu, X.-X.; Wang, G.; Lin, L.-L.; Feng, X.-M. Acta Chim. Sinica 2014, 72, 856 (in Chinese). (谢明胜, 武晓霞, 王刚, 林丽丽, 冯小明, 化学学报, 2014, 72, 856.)
[6] Nakajima, M.; Saito, M.; Hashimoto, S. Chem. Pharm. Bull. 2000, 48, 306.
[7] Hrdina, R.; Valterová, I.; Hoda?ová, J.; Císa?ová, I.; Kotora, M. Adv. Synth. Catal. 2007, 349, 822.
[8] Kadlcikova, A.; Hrdina, R.; Valterová, I.; Kotora, M. Adv. Synth. Catal. 2009, 351, 1279.
[9] Vlasaná, K.; Hrdina, R.; Valterová, I.; Kotora, M. Eur. J. Org. Chem. 2010, 36, 7040.
[10] Hrdina, R.; Kadlcikova, A.; Valterová, I.; Hoda?ová, J.; Kotora, M. Tetrahedron: Asymmetry 2006, 17, 3185.
[11] Hrdina, R.; Dra?ínský, M.; Valterová, I.; Hoda?ová, J.; Císa?ová, I.; Kotora, M. Adv. Synth. Catal. 2008, 350, 1449.
[12] Kadlcikova, A.; Valterová, I.; Duchácková, L.; Roithová J.; Kotora, M. Chem. Eur. J. 2010, 16, 9442.
[13] Motloch, P.; Valterová, I.; Kotora, M. Adv. Synth. Catal. 2014, 356, 199
[14] Shimada, T.; Kina, A.; Ikeda, S.; Hayashi, T. Org. Lett. 2002, 4, 2799.
[15] Shimada, T.; Kina, A.; Hayashi, T. J. Org. Chem. 2003, 68, 6329.
[16] Kina, A.; Shimada, T.; Hayashi, T. Adv. Synth. Catal. 2004, 346, 1169.
[17] Malkov, A. V.; Orsini, M.; Pernazza, D.; Muir, K. W.; Langer, V.; Meghani, P.; Ko?ovský, P. Org. Lett. 2002, 4, 1047.
[18] Malkov, A. V.; Bell, M.; Orsini, M.; Pernazza, D.; Massa, A.; Herrmann, P.; Meghani, P.; Ko?ovský, P. J. Org. Chem. 2003, 68, 9659.
[19] Malkov, A. V.; Bell, M.; Vassieu1, M.; Bugatti, V.; Ko?ovský, P. J. Mol. Catal. A: Chem. 2003, 196, 179.
[20] Malkov, A. V.; Bell, M.; Castelluzzo, F.; Ko?ovský, P. Org. Lett. 2005, 7, 3219.
[21] Malkov, A. V.; Westwater, M. M.; Gutnov, A.; Ramírez-López, P.; Friscourt, F.; Kadl?íková, A.; Hoda?ová, J.; Rankovic, Z.; Kotora, M.; Ko?ovský, P. Tetrahedron 2008, 64, 11335.
[22] Malkov, A. V.; Bar?óg, M.; Jewkes, Y.; Mikusek, J.; Kocovský, P. J. Org. Chem. 2011, 76, 4800.
[23] Malkov, A. V.; Dufková, L.; Farrugia, L.; Ko?ovský, P. Angew. Chem., Int. Ed. 2003, 42, 3674.
[24] Malkov, A.V.; Ramírez-López, P.; Biedermannová, L.; Rulísek, L.; Dufková L.; Kotora, M.; Zhu, F. J.; Ko?ovský, P. J. Am. Chem. Soc. 2008, 130, 5341.
[25] Malkov, A. V.; Kysilka, O.; Edgar, M.; Kadl?íková, A.; Kotora, M.; Ko?ovský, P. A. Chem. Eur. J. 2011, 17, 7162.
[26] Malkov, A.V.; Ston?ius, S.; Bell, M.; Castelluzzo, F.; Ramírez- López, P.; Biedermannová, L.; Langer, V.; Rulíšek, L.; Ko?ovskýl, P. Chem. Eur. J. 2013, 19, 9167.
[27] Zhao, H. W.; Yue, Y. Y.; Li, H. L.; Sheng, Z. H.; Yang, Z.; Meng, W. Chin. J. Chem. 2013, 31, 485.
[28] Bai, B.; Shen, L.; Ren, J.; Zhu, H. J. Adv. Synth. Catal. 2012, 354, 354.
[29] Bai, B.; Zhu, H. J.; Pan, W. Tetrahedron. 2012, 68, 6829.
[30] Deng, Y.; Pan, W.; Pei, Y. N.; Li, J. L.; Bai, B.; Zhu, H. J. Tetrahedron 2013, 69, 10431.
[31] Chelucci, G.; Belmonte, N.; Benagliab, M.; Pignataro, L. Tetrahedron Lett. 2007, 48, 4037.
[32] Chai, Q.; Song, C.; Sun, Z. J.; Ma, Y. D.; Ma, C. Q.; Dai, Y.; Andrus, M. B. Tetrahedron Lett. 2006, 47, 8611.
[33] Naicker, T.; Arvidsson, P. I.; Kruger, H. G.; Maguire, G. E. M.; Govender, T. Eur. J. Org. Chem. 2011, 34, 6923.
[34] Gnanamani, E.; Someshwar, N.; Ramanathan, C. R. Adv. Synth. Catal. 2012, 354, 2101.
[35] Wong, W. L.; Lee, C. S.; Leung, H. K.; Kwong, H. L. Org Biomol Chem. 2004, 14, 1967.
[36] Denmark, S. E.; Fan, Y. J. Am. Chem. Soc. 2002, 124,4233.
[37] Denmark, S. E.; Fan, Y.; Eastgate, M, D. J. Org. Chem. 2005, 70, 5235.
[38] Denmark, S. E.; Fan, Yu. Tetrahedron: Asymmetry 2006, 17, 687.
[39] Nakajima, M.; Yokota, T.; Saito, M.; Hashimoto, S. Tetrahedron Lett. 2004, 45, 61.
[40] Denmark, S. E.; Barsanti, P. A.; Wong, K. T.; Stavenger, R. A. J. Org. Chem. 1998, 63, 2428.
[41] Nakajima, M.; Saito, M.; Uemura, M.; Hashimoto, S. Tetrahedron Lett. 2002, 43, 8827.
[42] Chelucci, G.; Baldino, S.; Pinna, G. A.; Benaglia, M.; Laura, B.; Guizzetti, S. Tetrahedron 2008, 64, 7574.
[43] Takenaka, N.; Sarangthem, R. S.; Captain, B. Angew. Chem. 2008, 120, 9854.
[44] Chen, J. S.; Takenaka, N. Chem. Eur. J. 2009, 15, 7268.
[45] Gnanamani, E.; Someshwar, N.; Sanjeevi, J.; Ramanathan, C. R. Adv. Synth. Catal. 2014, 356, 2219.
[46] Pan, W.; Deng, Yu.; He, J. B.; Bai, B.; Zhu, H. J. Tetrahedron 2013, 69, 7253.
[47] Pei, Y. N.; Deng, Y.; Li, J. L.; Liu, L.; Zhu, H. J. Tetrahedron Lett. 2014, 55, 2948.
[48] Nakajima, M.; Saito, M.; Hashimoto, S. Tetrahedron: Asymmetry 2002, 13, 2449.
[49] Chen, J. S.; Captain, B.; Takenaka, N. Org. Lett. 2011, 13, 1654.
[50] Lu, T. X; Zhu, R. X.; An, Y.; Wheeler, S. E. J. Am. Chem. Soc. 2012, 134, 3095.
[51] Oh, K.; Ryu, J. Tetrahedron Lett. 2008, 49, 1935.

氮氧化物有机小分子催化剂在不对称反应中的应用

Application of N-Oxides as Organocatalysts in Asymmetric Reaction

PDF

Knowledge

Cited

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Shuang Yang, Xinqiang Fang. Kinetic Resolutions Enabled by N-Heterocyclic Carbene Catalysis: An Update [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 448-480.
[2]	Wanting Chen, Xiongwei Zhong, Jiale Xing, Changshu Wu, Yang Gao. Progress in Asymmetric Catalytic Synthesis of C—N Axis Chiral Compounds [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 349-377.
[3]	Quanbin Jiang. Progress in Synthesis of Axially Chiral Compounds through aza-Vinylidene o-Quinone Methide Intermediates [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 159-172.
[4]	Chun-Xia Cheng, Lu-Ping Wu, Feng Sha, Xin-Yan Wu. Enantioselective Vinylogous Allylic Alkylation of Coumarins with Morita-Baylis-Hillman Carbonates Catalyzed by Chiral Phosphine-Amide [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3188-3195.
[5]	Cheng Luo, Yanli Yin, Zhiyong Jiang. Recent Advances in Asymmetric Synthesis of P-Chiral Phosphine Oxides [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 1963-1976.
[6]	Haiqing Wang, Shuang Yang, Yuchen Zhang, Feng Shi. Advances in Catalytic Asymmetric Reactions Involving o-Hydroxybenzyl Alcohols [J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 974-999.
[7]	Weidi Cao, Xiaohua Liu. Recent Advances on Catalytic Enantioselective Protonation for Construction of α-Tertiary Carbonyl Compounds [J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 961-973.
[8]	Siqiang Fang, Zanjiao Liu, Tianli Wang. Recent Advances of the Atherton-Todd Reaction [J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 1069-1083.
[9]	Jiayi Zhao, Yicong Ge, Chuan He. Construction of Silicon-Stereogenic Center via Catalytic Asymmetric Si—H/X—H Dehydrogenative Coupling [J]. Chinese Journal of Organic Chemistry, 2023, 43(10): 3352-3366.
[10]	Yan Zeng, Fei Ye. Research Progress on New Catalytic Reaction Systems for Asymmetric Synthesis of Silicon-Stereogenic Center Containing Compounds [J]. Chinese Journal of Organic Chemistry, 2023, 43(10): 3388-3413.
[11]	Xin Kuang, Changhua Ding, Yichen Wu, Peng Wang. Catalytic Enantioselective Preparation of Chiral Allylsilanes [J]. Chinese Journal of Organic Chemistry, 2023, 43(10): 3367-3387.
[12]	Zengjin Dai, Xumu Zhang, Qin Yin. Advances on Asymmetric Reductive Amination with Ammonium Salts as Amine Sources [J]. Chinese Journal of Organic Chemistry, 2022, 42(8): 2261-2274.
[13]	Hui Li, Liang Yin. Research Progress of Copper-Catalyzed Direct Vinylogous Reactions [J]. Chinese Journal of Organic Chemistry, 2022, 42(6): 1573-1585.
[14]	Mengmeng Xu, Quan Cai. Progress of Catalytic Asymmetric Diels-Alder Reactions of 2-Pyrones [J]. Chinese Journal of Organic Chemistry, 2022, 42(3): 698-713.
[15]	Yunrong Chen, Wei Liu, Xiaoyu Yang. Recent Advances in Kinetic Resolution of Tertiary Alcohols [J]. Chinese Journal of Organic Chemistry, 2022, 42(3): 679-697.