Advances in Chiral Synthesis of 2-Aryl-2H-chromene Derivatives

doi:10.6023/cjoc202507004

Chinese Journal of Organic Chemistry ›› 2026, Vol. 46 ›› Issue (3): 773-785.DOI: 10.6023/cjoc202507004 Previous Articles Next Articles

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2-芳基-2H-色烯类化合物的手性合成研究进展

周顺丽^a^,^†, 刘继^a^,^†, 雷婷^a^,^b^,^*(), 杨斌全^a^,^*(), 江世智^a^,^b^,^*()

^a 大理大学药学院云南大理 671000
^b 云南省滇西抗病原植物资源筛选研究重点实验室云南大理 671000

收稿日期:2025-07-02 修回日期:2025-11-03 发布日期:2025-12-09
通讯作者: 雷婷, 杨斌全, 江世智
作者简介:
†共同第一作者
基金资助:
国家自然科学基金(22361002); 云南省高校服务重点产业科技项目(FWCY-ZNT2024023); 云南省地方本科高校基础研究联合专项(202101AO070315); 及云南省科技厅基础研究专项(202201AT070175); 及云南省科技厅基础研究专项(202401AT070071)

Advances in Chiral Synthesis of 2-Aryl-2H-chromene Derivatives

Shunli Zhou^a, Ji Liu^a, Ting Lei^a^,^b^,^*(), Binquan Yang^a^,^*(), Shizhi Jiang^a^,^b^,^*()

^a College of Pharmacy, Dali University, Dali, Yunan 671000
^b Yunnan Key Laboratory of Screening and Research on Anti-pathogenic Plant Resources from West Yunnan, Dali University, Dali, Yunan 671000

Received:2025-07-02 Revised:2025-11-03 Published:2025-12-09
Contact: Ting Lei, Binquan Yang, Shizhi Jiang
About author:
†These authors contributed equally to this work.
Supported by:
National Natural Science Foundation of China(22361002); Key Industry Science and Technology Projects for University Services in Yunnan Province(FWCY-ZNT2024023); Joint Special Fund Project for Basic Research of Local Undergraduate Universities in Yunnan Province(202101AO070315); Basic Research Special Project of Yunnan Provincial Department of Science and Technology(202201AT070175); Basic Research Special Project of Yunnan Provincial Department of Science and Technology(202401AT070071)

Chiral chromene structures are crucial components of numerous natural products and biologically active molecules. As a type of chromene, 2H-chromene is also an important representative of oxygen-containing heterocyclic compounds. It not only widely exists in natural products, pharmaceuticals, and bio-related molecules, but also has extensive applications in materials science and organic synthesis. Among them, chiral 2-aryl-2H-chromene derivatives not only exhibit broad pharmacological activities, but also serve as key intermediates for the synthesis of many active natural products, thus holding significant research value in fields such as medicinal chemistry and synthetic chemistry. The enantiomers of chiral compounds or chiral drugs often exhibit distinct physiological activities in living organisms. Since “The Thalidomide Tragedy”, the growing emphasis on chiral synthesis in organic chemistry has been paralleled by the pharmaceutical industry’s adoption of high optical purity as a key benchmark for drug quality and therapeutic performance. Therefore, the research on chiral drugs is of great significance, and meanwhile, the synthesis of chiral compounds has also attracted considerable attention from synthetic researchers. The research progress in the chiral synthesis of 2-aryl-2H-chromene compounds in recent years is summarized, mainly introducing three chiral synthesis methods for such chiral compounds, namely chemical resolution, kinetic resolution, and asymmetric catalysis involving chiral metal complexes or small organic molecules. Additionally, the future development of this field is prospected.

Key words: 2-aryl-2H-chromene, chiral synthesis, chiral metal complex catalysis, organic small molecule catalysis, research progress

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Shunli Zhou, Ji Liu, Ting Lei, Binquan Yang, Shizhi Jiang. Advances in Chiral Synthesis of 2-Aryl-2H-chromene Derivatives[J]. Chinese Journal of Organic Chemistry, 2026, 46(3): 773-785.

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Fig. & Tab. 25

Scheme 1. Chemical resolution strategy of (S)-(＋)-α-methoxyphenylacetic acid by Liu’s group

Scheme 2. Strategy with sharpless asymmetric epoxidation as the key reaction by Doris’s group

Scheme 3. Catalytic dehydration strategy with chiral benzylamine ligands by Park’s group

Scheme 4. Kinetic resolution strategy of chiral thiourea-based bifunctional organocatalysts developed by Xie’s group

Scheme 5. Asymmetric addition kinetic resolution strategy catalyzed by chiral β-amino alcohols by Park’s group

Scheme 6. N-Heterocyclic carbene (NHC) catalyzed Michael addition strategy by Maji’s group

Scheme 7. Kinetic resolution strategy by chiral Rh metal complex catalyzed asymmetric hydroarylation by Wang’s group

Scheme 8. Kinetic resolution strategy of rhodium catalyzed asymmetric hydrogenation by Hou’s group

Scheme 9. Asymmetric addition strategy catalyzed by the [(salen)Cr(SbF₆)] complex developed by Scheidt’s group

Scheme 10. Iridium-catalyzed intermolecular asymmetric allylation strategy by You’s group

Scheme 11. Palladium-catalyzed intramolecular asymmetric allylation strategy by Scheidt’s group

Scheme 12. Asymmetric Redox-Relay Heck reaction strategy by Hou’s group

Scheme 13. Strategy of one pot oxa-Michael-Aldol reaction catalyzed by chiral prolinol derivatives by Wang’s group

Scheme 14. Chiral secondary amine-catalyzed oxa-Michael-Henry reaction strategy for prolinol derivatives by Xu’s group

Scheme 15. Strategy of tandem oxa-Michael-Aldol reaction catalyzed by the combined catalyst by Xu’s group

Scheme 16. Asymmetric addition strategy catalyzed by the synergy of chiral brønsted acid and chiral lewis acid by Schaus’s group

Scheme 17. Strategy of the oxa-Michael-Aldol reaction catalyzed by chiral diarylprolinol silyl ether by Xu’s group

Scheme 18. Strategy of bifunctional chiral thiourea catalyzed oxa-Michael-aza-Henry-desulfonamidation tandem reaction by Schreiner’s group

Scheme 19. Strategy of chiral organic contact ion pair-catalyzed asymmetric allylic substitution reaction by Rueping’s group

Scheme 20. Strategy of oxa-Michael-Henry reaction catalyzed by 4-hydroxyprolinamide by Chen’s group

Scheme 21. Strategy for enantioselective selenocyclization and intramolecular ring-opening catalyzed by chiral squaramides by Jacobsen’s group

Scheme 22. Strategy of chiral phosphoramide catalyzed asymmetric sulfenylium ions and intramolecular ring-opening reactions by Denmark’s group

Scheme 23. Strategy of simple chiral prolinamide-based small-molecule catalyzed oxa-Michael-Henry reaction by Mohanta’s group

Scheme 24. Chiral L-prolinamide catalyzed aqueous oxa-Michael-Henry reaction strategy by Agarwal’s group

Scheme 25. Asymmetric catalysis strategy of oxa-Michael-Aldol reaction by chiral cyclohexanediamine-based small molecules by Li’s group

References 45

[46]	Rani, D.; Gulati, V.; Guleria, M.; Singh, S. P.; Agarwal, J. J. Mol. Struct. 2022, 1265, 133341.
[47]	Li, C. L.; Chen, C. X.; Zhan, M. R.; Wang, Z. X.; Wang, S. Y. Russ. J. Org. Chem. 2024, 60, S140.
[1]	Risi, C.; Zhao, F.; Castagnolo, D. ACS Catal. 2019, 9, 7264.
[2]	Kaur, N. Curr. Org. Synth. 2017, 14, 531.
[3]	Ellis, G. P. Textbook of Chemistry of Heterocyclic Compounds, Wiley-Interscience, New York, 1977, 31.
[4]	Ellis, G. P.; Lockhart, I. M. Chem. Heterocycl. Compd. 1981, 36.
[5]	Pratap, R.; Ram, V. J. Chem. Rev. 2014, 114, 10476.
[6]	Ruth, B.; Jeremy, Q.; Peter, K. Nat. Rev. Drug Discovery 2003, 2, 177.
[7]	Thakor, V.; Poddar, M.; Dey, S.; Manjula, S. N.; Madhunapantula, S. V.; Pawara, R.; Patel, H. M.; Noolvi, M. N. RSC Adv. 2016, 6, 79166.
[8]	Nicolaou, K. C.; Pfefferkorn, J. A.; Mitchell, H. J.; Roecker, A. J.; Barluenga, S.; Cao, G. Q.; Affleck, R. L.; Lillig, J. E. J. Am. Chem. Soc. 2000, 122, 9954.
[9]	Aponick, A.; Biannic, B.; Jong, M. R. Chem. Commun. 2010, 46, 6849.
[10]	Zhao, Y. J. MS Thesis, Fujian Agriculture and Forestry University, Fuzhou, 2017 (in Chinese).
	(赵旻骏, 硕士论文, 福建农林大学, 福州, 2017.)
[11]	Banerjee, D.; Kayal, U. Tetrahedron Lett. 2016, 57, 1667.
[12]	Ishizuka, N.; Matsumura, K. I.; Sakai, K. J. Med. Chem. 2002, 45, 2041.
[13]	Yu, P.; Cen, P. L.; Li, J. R. China Biotechnol. 2001, 21, 89 (in Chinese).
	(于平, 岑沛霖, 励建荣, 中国生物工程杂志, 2001, 21, 89.)
[14]	Yin, S. Q.; Zhang, C. F.; Mao, X.; Liu, Z. P. Tetrahedron: Asymmetry 2013, 24, 320.
[15]	Hardouin, C.; Burgaud, L.; Valleix, A.; Doris, E. Tetrahedron Lett. 2003, 44, 435.
[16]	Farina, V.; Krishnan, B. J. Am. Chem. Soc. 1991, 113, 9585.
[17]	Pfenninger, A. Synthesis 1986, 89.
[18]	Kim, D. J.; Lee, Y. M.; Choi, E. T.; Lee, M. H.; Park, Y. S. Bull. Korean Chem. Soc. 2009, 30, 1211.
[19]	Xie, J. W.; Fan, L. P.; Su, H.; Li, X. S.; Xu, D. C. Org. Biomol. Chem. 2010, 8, 2117.
[20]	Kang, S.; Baek, J.; Ko, Y.; Im, C.; Park, K. Synlett 2013, 24, 630.
[21]	Maji, B.; Bhattacharaya, A.; Shukla, P. M.; Kaushik, L. K. Org. Chem. Front. 2019, 6, 3523.
[22]	Yang, Q. J.; Wang, Y. B.; Luo, S. H.; Wang, J. Angew. Chem., Int. Ed. 2019, 58, 5343.
[23]	(a) Bauer, D. J.; Selway, J. W. T.; Batchelor, J. F.; Tisdale, M.; Caldwell, I. C.; Young, D. A. B. Nature 1981, 292, 369.
	(b) Quaglia, M. G.; Desideri, N.; Bossù E.; Sestili, I.; Conti, C. Chirality 1992, 4, 65.
[24]	Su, Y. H.; Xie, C. C.; Hu, Z. Y.; Zi, G. F.; Li, C. Y.; Hou, G. H. Org. Lett. 2025, 27, 3095.
[25]	David, J.; Maloney, J. Z. D.; Shelley, R.; Starck, Z. G.; Sidney, M. H. J. Am. Chem. Soc. 2005, 127, 4140.
[26]	Harathi, D. S.; Prantik, M.; Glenn, P. A. Y.; Mary, P. W. J. Org. Chem. 2015, 80, 4003.
[27]	Majumdar, N.; Paul, N. D.; Mandal, S.; Bruin, B.; Wulff, W. D. ACS Catal. 2015, 5, 2329.
[28]	Teller, H.; Corbet, M.; Mantilli, L.; Gopakumar, G.; Goddard, R.; Thiel, W.; Furstner, A. J. Am. Chem. Soc. 2012, 134, 15331.
[29]	Reynolds, T. E.; Scheidt, K. A. Angew. Chem., Int. Ed. 2007, 46, 7806.
[30]	He, H.; Ye, K. Y.; Wu, Q. F.; Dai, L. X.; You, S. L. Adv. Synth. Catal. 2012, 354, 1084.
[31]	Zeng, B. S.; Yu, X. Y.; Siu, P. W.; Scheidt, K. A. Chem. Sci. 2014, 5, 2277.
[32]	Jiang, Z. Z.; Gao, A.; Li, H.; Chen, D.; Ding, C. H.; Xu, B.; Hou, X. L. Chem.-Asian. J. 2017, 12, 3119.
[33]	Wang, J. Q.; Crane, E. A.; Scheidt, K. A. Org. Lett. 2011, 13, 3086.
[34]	Rueping, M.; Nachtsheim, B. J.; Ieawsuwan, W.; Atodiresei, I. Angew. Chem., Int. Ed. 2011, 50, 6706.
[35]	Li, H.; Wang, J.; E-Nunu, T.; Zu, L.; Jiang, W.; Wei, S. H.; Wang, W. Chem. Commun. 2007, 507.
[36]	Xu, D. Q.; Wang, Y. F.; Luo, S. P.; Zhang, S.; Zhong, A. G.; Chen, H.; Xu, Z. Y. Adv. Synth. Catal. 2008, 350, 2610.
[37]	Luo, S. P.; Li, Z. B.; Wang, L. P.; Guo, Y. X.; Xia, A. B.; Xu, D. Q. Org. Biomol. Chem. 2009, 7, 4539.
[38]	Moquist, P. N.; Kodama, T.; Schaus, S. E. Angew. Chem., Int. Ed. 2010, 49, 7096.
[39]	Shen, H.; Yang, K. F.; Shi, Z. H.; Jiang, J. X.; Lai, J. Q.; Xu, L. W. Eur. J. Org. Chem. 2011, 2011, 5031.
[40]	Zhang, Z. G.; Jakab, G.; Schreiner, P. R. Synlett 2011, 1262.
[41]	Rueping, M.; Uria, U.; Lin, M. Y.; Atodiresei, I. J. Am. Chem. Soc. 2011, 133, 3732.
[42]	Yin, G. H.; Zhang, R. C.; Lei, L.; Tan, J.; Chen, L. G. Eur. J. Org. Chem. 2013, 2013, 5431.
[43]	Hu, Z.; Song, L.; Jacobsen, E. N. J. Am. Chem. Soc. 2014, 136, 16485.
[44]	Denmark, S. E.; Kornfilt, D. J. Org. Chem. 2017, 82, 3192.
[45]	Mohanta, R.; Bez, G. J. Org. Chem. 2020, 85, 4627.

2-芳基-2H-色烯类化合物的手性合成研究进展

Advances in Chiral Synthesis of 2-Aryl-2H-chromene Derivatives

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