Applications of Helicenes and Their Derivatives in Asymmetric Catalysis

doi:10.6023/cjoc201710028

Chin. J. Org. Chem. ›› 2018, Vol. 38 ›› Issue (3): 541-554.DOI: 10.6023/cjoc201710028 Previous Articles Next Articles

Special Issue: 有机超分子化学合辑

Reviews

螺烯及其衍生物在不对称催化中的应用

房蕾^a,b, 林伟彬^a,b, 沈赟^a, 陈传峰^a,b

a 中国科学院化学研究所分子识别与功能院重点实验室北京 100190;
b 中国科学院大学北京 100049

收稿日期:2017-10-24 修回日期:2017-11-16 发布日期:2017-11-28
通讯作者: 陈传峰,E-mail:cchen@iccas.ac.cn E-mail:cchen@iccas.ac.cn
基金资助:
国家自然科学基金（Nos.21572233，51373180）和中国科学院先导（No.XDB12010400）资助项目.

Applications of Helicenes and Their Derivatives in Asymmetric Catalysis

Fang Lei^a,b, Lin Weibin^a,b, Shen Yun^a, Chen Chuanfeng^a,b

a Key Laboratory of Molecular Recognition and Functions, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190;
b University of Chinese Academy of Sciences, Beijing 100049

Received:2017-10-24 Revised:2017-11-16 Published:2017-11-28
Contact: 10.6023/cjoc201710028 E-mail:cchen@iccas.ac.cn
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21572233, 51373180), and the Strategic Priority Research Program of Chinese Academy of Sciences (No. XDB12010400).

Helicenes are a kind of π-conjugated helical compounds which are consisted of ortho-fused benzene or other aromatic rings. Compared to other kinds of chiral catalysts, studies on helicene-based catalysts with helical chirality showed late start and lagging development. However, since helicene molecules exhibit structural rigidity, thermal stability, easily functionalization, and excellent chiral environment for asymmetric catalysis by continuous elaborate curve in three-dimensional space, investigation on the synthesis of helicene-based chiral catalysts and their applications in asymmetric catalysis have attracted increasing interest in recent years. According to the different roles of the helicenes played in the asymmetric catalysis, the helicene-based catalysts can be classified into chiral inducers, helically chiral ligands and helical organocatalysts, and their applications in asymmetric catalysis will be focused on in this review, respectively.

Key words: helicene, asymmetric catalysis, chiral induction, helical ligand, organocatalyst

Cite this article

Fang Lei, Lin Weibin, Shen Yun, Chen Chuanfeng. Applications of Helicenes and Their Derivatives in Asymmetric Catalysis[J]. Chin. J. Org. Chem., 2018, 38(3): 541-554.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Knowles, W. S.; Sabacky, M. J. Chem. Commun. 1968, 1445-1446.
[2] Ding, K.-L.; Fan, Q.-H. Asymmetric Catalysis:New Concepts and Methods, Chemical Industry Press, Beijing, 2009 (in Chinese). (丁奎岭, 范青华, 不对称催化新概念与新方法, 化学工业出版社, 北京, 2009.)
[3] Lin, G.-Q.; Sun, X.-W.; Chen, Y.-Q.; Li, Y.-M.; Chan, A. S. C. Chiral Synthesis——Principles and Application of Asymmetric Reaction, Science Press, Beijing, 2013 (in Chinese). (林国强, 孙兴文, 陈耀全, 李月明, 陈新滋, 手性合成:不对称反应及其应用, 第五版, 科学出版社, 北京, 2013.)
[4] Shen, Y.; Chen, C.-F. Chem. Rev. 2012, 112, 1463.
[5] Gingras, M. Chem. Soc. Rev. 2013, 42, 1051.
[6] Ben Hassine, B.; Gorsane, M.; Geerts-Evrard, F.; Pecher, J.; Martin, R. H.; Castelet, D. Bull. Soc. Chim. Belg. 1986, 95, 547.
[7] Ben Hassine, B.; Gorsane, M.; Pecher, J.; Martin, R. H. Bull. Soc. Chim. Belg. 1987, 96, 801.
[8] Hassine, B. B.; Gorsane, M.; Pecher, J.; Martin, R. H. Bull. Soc. Chim. Belg. 1985, 94, 759.
[9] Benhassine, B.; Gorsane, M.; Pecher, J.; Martin, R. H. Bull. Soc. Chim. Belg. 1986, 95, 557.
[10] Ben Hassine, B.; Gorsane, M.; Pecher, J.; Martin, R. H. Bull. Soc. Chim. Belg. 1985, 94, 597.
[11] Reetz, M. T.; Beuttenmüller, E. W.; Goddard, R. Tetrahedron Lett. 1997, 38, 3211.
[12] Sato, I.; Urabe, H.; Ishiguro, S.; Shibata, T.; Soai, K. Angew. Chem. 2003, 115, 329.
[13] Soai, K.; Shibata, T.; Morioka, H.; Choji, K. Nature 1995, 378, 767.
[14] Sato, I.; Sugie, R.; Matsueda, Y.; Furumura, Y.; Soai, K. Angew. Chem., Int. Ed. 2004, 43, 4490.
[15] Kawasaki, T.; Matsumura, Y.; Tsutsumi, T.; Suzuki, K.; Ito, M.; Soai, K. Science 2009, 324, 492.
[16] Shindo, H.; Shirota, Y.; Niki, K.; Kawasaki, T.; Suzuki, K.; Araki, Y.; Matsumoto, A.; Soai, K. Angew. Chem., Int. Ed. 2013, 52, 9135.
[17] Soai, K.; Sato, I.; Shibata, T. Chem. Rec. 2001, 1, 321.
[18] Kawasaki, T.; Suzuki, K.; Licandro, E.; Bossi, A.; Maiorana, S.; Soai, K. Tetrahedron:Asymmetry 2006, 17, 2050.
[19] Sato, I.; Yamashima, R.; Kadowaki, K.; Yamamoto, J.; Shibata, T.; Soai, K. Angew. Chem., Int. Ed. 2001, 40, 1096.
[20] Matsumoto, A.; Yonemitsu, K.; Ozaki, H.; Misek, J.; Stary, I.; Stara, I. G.; Soai, K. Org. Biomol. Chem. 2017, 15, 1321.
[21] Reetz, M. T.; Sostmann, S. J. Organomet. Chem. 2000, 603, 105.
[22] Monteforte, M.; Cauteruccio, S.; Maiorana, S.; Benincori, T.; Forni, A.; Raimondi, L.; Graiff, C.; Tiripicchio, A.; Stephenson, G. R.; Licandro, E. Eur. J. Org. Chem. 2011, 5649.
[23] Yamamoto, K.; Shimizu, T.; Igawa, K.; Tomooka, K.; Hirai, G.; Suemune, H.; Usui, K. Sci. Rep. 2016, 6, 36211.
[24] Nakano, D.; Hirano, R.; Yamaguchi, M.; Kabuto, C. Tetrahedron Lett. 2003, 44, 3683.
[25] Nakano, D.; Yamaguchi, M. Tetrahedron Lett. 2003, 44, 4969.
[26] Sehnal, P.; Krausová, Z.; Teplý, F.; Stará, I. G.; Starý, I.; Rulíšek, L.; Šaman, D.; Císarová, I. J. Org. Chem. 2008, 73, 2074.
[27] Krausová, Z.; Sehnal, P.; Bondzic, B. P.; Chercheja, S.; Eilbracht, P.; Stará, I. G.; Šaman, D.; Starý, I. Eur. J. Org. Chem. 2011, 3849.
[28] Tsujihara, T.; Inada-Nozaki, N.; Takehara, T.; Zhou, D.-Y.; Suzuki, T.; Kawano, T. Eur. J. Org. Chem. 2016, 4948.
[29] Yavari, K.; Moussa, S.; Ben Hassine, B.; Retailleau, P.; Voituriez, A.; Marinetti, A. Angew. Chem., Int. Ed. 2012, 51, 6748.
[30] Yavari, K.; Retailleau, P.; Voituriez, A.; Marinetti, A. Chem.-Eur. J. 2013, 19, 9939.
[31] Aillard, P.; Retailleau, P.; Voituriez, A.; Marinetti, A. Chem. Commun. 2014, 50, 2199.
[32] Yavari, K.; Aillard, P.; Zhang, Y.; Nuter, F.; Retailleau, P.; Voituriez, A.; Marinetti, A. Angew. Chem., Int. Ed. 2014, 53, 861.
[33] Aillard, P.; Voituriez, A.; Dova, D.; Cauteruccio, S.; Licandro, E.; Marinetti, A. Chem.-Eur. J. 2014, 20, 12373.
[34] Aillard, P.; Retailleau, P.; Voituriez, A.; Marinetti, A. Chem.-Eur. J. 2015, 21, 11989.
[35] Aillard, P.; Dova, D.; Magne, V.; Retailleau, P.; Cauteruccio, S.; Licandro, E.; Voituriez, A.; Marinetti, A. Chem. Commun. 2016, 52, 10984.
[36] Dreher, S. D.; Thomas, J.; Katz, T. J.; Lam, K. C.; Rheingold, A. L. J. Org. Chem. 2000, 65, 815.
[37] Okubo, H.; Yamaguchi, M.; Kabuto, C. J. Org. Chem. 1998, 63, 9500.
[38] Takenaka, N.; Sarangthem, R. S.; Captain, B. Angew. Chem., Int. Ed. 2008, 47, 9708.
[39] Chen, J.; Captain, B.; Takenaka, N. Org. Lett. 2011, 13, 1654.
[40] Takenaka, N.; Chen, J.; Captain, B.; Sarangthem, R. S.; Chandrakumar, A. J. Am. Chem. Soc. 2010, 132, 4536.
[41] Narcis, M. J.; Sprague, D. J.; Captain, B.; Takenaka, N. Org. Biomol. Chem. 2012, 10, 9134.
[42] Misek, J.; Teply, F.; Stara, I. G.; Tichy, M.; Saman, D.; Cisarova, I.; Vojtisek, P.; Stary, I. Angew. Chem., Int. Ed. 2008, 47, 3188.
[43] Samal, M.; Misek, J.; Stara, I. G.; Stary, I. Collect. Czech. Chem. Commun. 2009, 74, 1151.
[44] Crittall, M. R.; Rzepa, H. S.; Carbery, D. R. Org. Lett. 2011, 13, 1250.
[45] Cauteruccio, S.; Dova, D.; Benaglia, M.; Genoni, A.; Orlandi, M.; Licandro, E. Eur. J. Org. Chem. 2014, 2694.
[46] Gicquel, M.; Zhang, Y.; Aillard, P.; Retailleau, P.; Voituriez, A.; Marinetti, A. Angew. Chem., Int. Ed. 2015, 54, 5470.

螺烯及其衍生物在不对称催化中的应用

Applications of Helicenes and Their Derivatives in Asymmetric Catalysis

PDF

Knowledge

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]	Tiantian Liu, Xinhong Duan. Recent Progress in the Construction of Chiral 3-Substituted Indoles by Asymmetric Friedel-Crafts Reactions [J]. Chinese Journal of Organic Chemistry, 2023, 43(11): 3695-3712.
[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]	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.
[12]	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.
[13]	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.
[14]	Shouyi Cen, Zhipeng Zhang. Synthesis of Biphenanthrol-Based Confined Chiral Phosphoric Acid [J]. Chinese Journal of Organic Chemistry, 2022, 42(8): 2574-2581.
[15]	Hui Li, Liang Yin. Research Progress of Copper-Catalyzed Direct Vinylogous Reactions [J]. Chinese Journal of Organic Chemistry, 2022, 42(6): 1573-1585.