Application of Bifunctional (Thio)ureas with Auxiliary in Asymmetric Organocatalysis

doi:10.6023/cjoc201508029

Chin. J. Org. Chem. ›› 2016, Vol. 36 ›› Issue (2): 306-314.DOI: 10.6023/cjoc201508029 Previous Articles Next Articles

Reviews

含辅助基的双功能(硫)脲催化剂在不对称有机催化中的应用

陈学伟^a,b, 辛玉娟^a,b, 刘青^a,b, 兰支利^a,b

a 湖南师范大学有机功能分子组装与应用重点实验室长沙 410081;
b 石化新材料与资源精细利用国家地方联合工程实验室湖南师范大学长沙 410081

收稿日期:2015-08-30 修回日期:2015-09-18 发布日期:2015-10-08
通讯作者: 陈学伟 E-mail:chenxuewei@yeah.net
基金资助:
国家自然科学基金(No. 20906029)资助项目

Application of Bifunctional (Thio)ureas with Auxiliary in Asymmetric Organocatalysis

Chen Xuewei^a,b, Xin Yujuan^a,b, Liu Qing^a,b, Lan Zhili^a,b

a Key Laboratory of the Assembly and Application of Organic Functional Molecules, Hunan Normal University, Changsha 410081;
b National & Local Joint Engineering Laboratory for New Petro-chemical Materials and Fine Utilization of Resources, Hunan Normal University, Changsha 410081

Received:2015-08-30 Revised:2015-09-18 Published:2015-10-08
Supported by:
Project supported by the National Natural Science Foundation of China (No. 20906029)

Chiral bifunctional (thio)ureas, which are made up of (thio)urea group, nucleophilic activation group and auxiliary, have attracted widespread attention in asymmetric organocatalysis research nowadays because of their easy control structure and excellent catalytic performance. The introduction of the activation group, which can greatly influence the catalytic performance of the catalyst, has become an important and concern research field for the catalyst design, while the introduction of suitable auxiliary can also be used to control and optimize catalytic performance, and become an important supplementary method. However, up to now, there is no systematical review exclusively on utilization of auxiliary strategy for the construction of chiral bifunctional (thio)ureas. In this paper, the research progress of the construction of chiral bifunctional (thio)ureas based on tunable achiral and chiral auxiliaries in recent years is reviewed. These catalysts can be successfully applied in a diverse variety of highly enantioselective transformations providing a wide range of versatile organic compounds. The influence of several factors in the auxiliaries, such as steric hindrance, chiral environment, electronic effect and hydrogen bond donor, on the catalytic performance is described. Besides, an outlook for future development of auxiliaries to construct bifunctional (thio)ureas is given.

Key words: bifunctional (thio)urea, auxiliary, asymmetric organocatalysis, application

Cite this article

Chen Xuewei, Xin Yujuan, Liu Qing, Lan Zhili. Application of Bifunctional (Thio)ureas with Auxiliary in Asymmetric Organocatalysis[J]. Chin. J. Org. Chem., 2016, 36(2): 306-314.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] (a) Taylor, M. S.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2006, 45, 1520. (b) Connon, S. J. Chem. Eur. J. 2006, 12, 5418. (c) Doyle, A. G.; Jacobsen, E. N. Chem. Rev. 2007, 107, 5713.
[2] Sigman, M. S.; Jacobsen, E. N. J. Am. Chem. Soc. 1998, 120, 4901.
[3] Okino, T.; Hoashi, Y.; Takemoto, Y. J. Am. Chem. Soc. 2003, 125, 12672.
[4] (a) Wu, Q.-H.; Gao, Y.-J.; Li, Z.; Wang, J.-M.; Wang, C.; Ma, J.-J.; Song, S.-J. Chin. J. Org. Chem. 2007, 27, 1491 (in Chinese). (吴秋华, 高勇军, 李芝, 王俊敏, 王春, 马晶军, 宋双居, 有机化学, 2007, 27, 1491.) (b) Miyabe, H.; Takemoto, Y. Bull. Chem. Soc. Jpn. 2008, 81, 785. (c) Yu, X.; Wang, W. Chem. Asian J. 2008, 3, 516. (d) Takemoto, Y. Chem. Pharm. Bull. 2010, 58, 593. (e) Sohtome, Y.; Nagasawa, K. Synlett 2010, 1. (f) Chai, Z.; Zhao, G. Catal. Sci. Technol. 2012, 2, 29. (g) Lu, L.-Q.; An, X.-L.; Chen, J.-R.; Xiao, W.-J. Synlett 2012, 490. (h) 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.)
[5] (a) Connon, S. J. Chem. Commun. 2008, 2499. (b) Siau, W. Y.; Wang, J. Catal. Sci. Technol. 2011, 1, 1298. (c) Tsakos, M.; Kokotos, C. G. Tetrahedron 2013, 69, 10199. (d) Serdyuk, O. V.; Heckel, C. M.; Tsogoeva, S. B. Org. Biomol. Chem. 2013, 11, 7051. (e) Zhang, Z.-G.; Schreiner, P. R. Chem. Soc. Rev. 2009, 38, 1187.
[6] (a) Zhang, Z.-H.; Dong, X.-Q.; Teng, H.-L.; Tao, H.-Y.; Wang, C.-J. Chin. Sci. Bull. 2009, 54, 3407 (in Chinese). (张志海, 董秀琴, 滕怀龙, 陶海燕, 王春江, 科学通报, 2009, 54, 3407.) (b) Fang, X.; Wang, C.-J. Chem. Commun. 2015, 51, 1185. (c) Narayanaperumal, S.; Rivera, D. G.; Silva, R. C.; Paixão, M. W. ChemCatChem 2013, 5, 2756.
[7] Lippert, K. M.; Hof, K.; Gerbig, D.; Ley, D.; Hausmann, H.; Guenther, S.; Schreiner, P. R. Eur. J. Org. Chem. 2012, 5919.
[8] Wei, Q.; Gong, L.-Z. Org. Lett. 2010, 12, 1008.
[9] He, T.; Qian, J.-Y.; Song, H.-L.; Wu, X.-Y. Synlett 2009, 3195.
[10] Ban, S.-R.; Zhu, X.-X.; Zhang, Z.-P.; Li, Q.-S. Eur. J. Org. Chem. 2013, 2977.
[11] Yu, L.; Li, P.-F. Tetrahedron Lett. 2014, 55, 3697.
[12] Li, J.; Yang, G.-X.; Cui, Y.-C. J. Appl. Polym. Sci. 2011, 121, 1506.
[13] Li, J.; Yang, G.-X.; Qin, Y.-Y.; Yang, X.-R.; Cui, Y.-C. Tetrahedron: Asymmetry 2011, 22, 613.
[14] Miura, T.; Nishida, S.; Masuda, A.; Tada, N.; Itoh, A. Tetrahedron Lett. 2011, 52, 4158.
[15] Tuchman-Shukron, L.; Miller, S, J.; Portnoy, M. Chem. Eur. J. 2012, 18, 2290.
[16] (a) Tsogoeva, S.-B.; Wei, S. Chem. Commun. 2006, 1451. (b) Yalalov, D. A.; Tsogoeva, S. B.; Schmatz, S. Adv. Synth. Catal. 2006, 348, 826.
[17] Wang, Y.-F.; Zhang, W.; Luo, S.-P.; Li, B.-L.; Xia, A.-B.; Zhong, A.-G.; Xu, D.-Q. Chem. Asian J. 2009, 4, 1834.
[18] Rao, K. S.; Trivedi, R.; Kantam, M. L. Synlett 2015, 221.
[19] Durmaz, M.; Sirit, A. Tetrahedron: Asymmetry 2013, 24, 1443.
[20] Lalonde, M. P.; Chen, Y.-G.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2006, 45, 6366.
[21] Lalonde, M. P.; McGowan, M. A.; Rajapaksa, N. S.; Jacobsen, E. N. J. Am. Chem. Soc. 2013, 135, 1891.
[22] Kokotos, C. G.; Kokotos, G. Adv. Synth. Catal. 2009, 351, 1355.
[23] Liu, K.; Cui, H.-F.; Nie, J.; Dong, K.-Y.; Li, X.-J.; Ma, J.-A. Org. Lett. 2007, 9, 923.
[24] Lu, A.-D.; Gao, P.; Wu, Y.; Wang, Y.-M.; Zhou, Z.-H.; Tang, C.-C. Org. Biomol. Chem. 2009, 7, 3141.
[25] Pu, X.-W.; Peng, F.-Z.; Zhang, H.-B.; Shao, Z.-H. Tetrahedron 2010, 66, 3655.
[26] Lu, A.-D.; Hu, K.-L.; Wang, Y.-M.; Song, H.-B.; Zhou, Z.-H.; Fang, J.-X.; Tang, C.-C. J. Org. Chem. 2012, 77, 6208.
[27] Jiang, X.-X.; Zhang, Y.-F.; Chan, A. S. C.; Wang, R. Org. Lett. 2009, 11, 153.
[28] Jiang, X.-X.; Cao, Y.-M.; Wang, Y.-Q.; Liu, L.-P.; Shen, F.-F.; Wang, R. J. Am. Chem. Soc. 2010, 132, 15328.
[29] Li, P.-F.; Wang, Y.-C.; Liang, X.-M.; Ye, J.-X. Chem. Commun. 2008, 44, 3302.
[30] Tan, B.; Candeias, N. R.; Barbas, C. F., III Nat. Chem. 2011, 3, 473.
[31] Ma, Z.-W.; Liu, Y.-X.; Zhang, W.-J.; Tao, Y.; Zhu, Y.; Tao, J.-C.; Tang, M. S. Eur. J. Org. Chem. 2011, 6747.
[32] Song, Z.-T.; Zhang, T.; Du, H.-L.; Ma, Z.-W.; Zhang, C.-H.; Tao, J.-C. Chirality 2014, 26, 121.
[33] Tzeng, Z.-H.; Chen, H.-Y.; Huang, C.-T.; Chen, K.-M. Tetrahedron Lett. 2008, 49, 4134.
[34] Wang, C.-J.; Zhang, Z.-H.; Dong, X.-Q.; Xue, Z.-Y.; Teng, H.-L. J. Am. Chem. Soc. 2008, 130, 8606.
[35] Wang, C.-J.; Zhang, Z.-H.; Dong, X.-Q.; Wu, X.-J. Chem. Commun. 2008, 44, 1431.
[36] Jones, C. R.; Panto?, G. D.; Morrison, A. J.; Smith, M. D. Angew. Chem., Int. Ed. 2009, 48, 7391.
[37] Deng, H.-P.; Shi, M. Eur. J. Org. Chem. 2012, 183.

含辅助基的双功能(硫)脲催化剂在不对称有机催化中的应用

Application of Bifunctional (Thio)ureas with Auxiliary in Asymmetric Organocatalysis

PDF

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Chunyan She, Anjing Wang, Shan Liu, Wenming Shu, Weichu Yu. Preparation of Phenacyl Azides and Their Application Advances in Organic Synthesis [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 481-507.
[2]	Shutong Zhou, Shengnan Tu, Zijian Gao, Yemei Wang, Shasha Sun. Research Progress in Synthesis, Properties and Application of Subphthalocyanine [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2628-2646.
[3]	Guangli Xu, Jing Xu, Haidong Xu, Xiang Cui, Xingzhong Shu. Research Progress of Transition Metal Catalyzed Synthesis of 1,3- Conjugated Diene Compounds from Alkenes and Alkynes [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 1899-1933.
[4]	Liangru Yang, Mengli Guo, Jinwei Yuan, Jiamei Wangx, Yuting Xia, Yongmei Xiao, Pu Mao. Research Progress on Pincer N-Heterocyclic Carbene Metal Complexes [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 2002-2025.
[5]	Yangyang Li, Xiaofei Sun, Xiaoling Hu, Yuanyuan Ren, Keli Zhong, Xiaomei Yan, Lijun Tang. Synthesis of Triphenylamine Derivative and Its Recognition for Hg²⁺ with “OFF-ON” Fluorescence Response Based on Aggregation-Induced Emission (AIE) Mechanism [J]. Chinese Journal of Organic Chemistry, 2023, 43(1): 320-325.
[6]	Lixin Ju, Qi Shao, Linchuan Lu, Hongfei Lu. A New Turn-On Fluorescent Chemosensor for Selective Detection of Al³⁺ Based on a Purine Schiff Base and Its Cell Imaging [J]. Chinese Journal of Organic Chemistry, 2022, 42(6): 1706-1712.
[7]	Xing Wang, Qianqian Song, Xuling Chen, Pengfei Li, Yunkun Qi, Wenjun Li. Organocatalytic Regio- and Enantioselective aza-1,8-Conjugate Additions of Isoxazol-5(4H)-ones to 6-Methide-6H-indoles [J]. Chinese Journal of Organic Chemistry, 2022, 42(6): 1722-1734.
[8]	Sihong Chen, Jiamin Xu, Yuemei Li, Baoru Peng, Lingyu Luo, Huiye Feng, Zhaohua Chen, Zhaoyang Wang. Research Progress of Aggregation-Caused Quenching (ACQ) to Aggregation-Induced Emission (AIE) Transformation Based on Organic Small Molecules [J]. Chinese Journal of Organic Chemistry, 2022, 42(6): 1651-1666.
[9]	Sihong Chen, Qi Chen, Shihe Luo, Xiying Cao, Guoxian Yang, Xiaoqing Zeng, Zhaoyang Wang. Progress in Design, Synthesis and Application of Triphenylamine-Based Fluorescent Probes [J]. Chinese Journal of Organic Chemistry, 2021, 41(3): 919-933.
[10]	Chaohui Cui, Yuting Liu, Ya Du. Recent Advancements of Hexaazatriphenylene-Based Materials for Energy Applications [J]. Chinese Journal of Organic Chemistry, 2021, 41(11): 4167-4179.
[11]	Han Ren, Ruxiang Li, Zhijian Chen, Lili Li, Hao Wang. Modification Methods and Applications of Self-Assembly Peptides [J]. Chinese Journal of Organic Chemistry, 2021, 41(10): 3983-3994.
[12]	Qiang Pei, Aixiang Ding, Jinjin Wu. Supramolecular Assemblies Based on Intramolecular Three-Center Hydrogen Bond and their Applications [J]. Chinese Journal of Organic Chemistry, 2021, 41(1): 105-125.
[13]	Cheng Xiaohong, Li Shuang, Wang Jingyang, Li Wangnan. “Turn-On” Fluorescent Probe for Hypochlorite: Successful Bioimaging and Real Application in Tap Water [J]. Chinese Journal of Organic Chemistry, 2020, 40(7): 1941-1947.
[14]	ChenZhang Pengfei, Lan Wenjie, Yu Xuan, Fu Bin. New Application of β,γ-Unsaturated α-Ketoesters in Asymmetric Catalysis [J]. Chinese Journal of Organic Chemistry, 2020, 40(6): 1448-1460.
[15]	Yu Qing, Chen Xiaoli, Liu Hua, Zhang Qilong. Recent Progress in Colorimetric and Fluorimetric Probes for the Detection of Hypochlorous Acid [J]. Chinese Journal of Organic Chemistry, 2020, 40(5): 1206-1231.