2-芳基-2H-色烯类化合物的手性合成研究进展

doi:10.6023/cjoc202507004

有机化学 ›› 2026, Vol. 46 ›› Issue (3): 773-785.DOI: 10.6023/cjoc202507004 上一篇下一篇

综述与进展

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)

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摘要/Abstract

色烯结构是许多天然产物和生物活性分子的重要组成部分, 2H-色烯作为色烯的一种, 同时也是氧杂环化合物的重要代表, 不仅广泛存在于天然产物、药剂和生物相关分子中, 而且在材料科学和有机合成中也有广泛的应用. 其中手性2-芳基-2H-色烯类化合物具有广泛的药理活性, 是合成众多活性天然产物的关键中间体, 在药物化学及合成化学等领域具有重要的研究价值. 手性化合物或手性药物的对映异构体在生物体内往往会表现出不同的生理活性, 自“反应停”事件以来, 在有机合成领域手性合成技术日益受到重视, 与此同时, 使用高光学纯度的药物已成为医药行业产品质量与疗效的关键指标. 因此, 手性药物的研究具有重要意义, 手性化合物的合成也备受合成工作者的关注. 归纳总结了近年来2-芳基-2H-色烯类化合物的手性合成研究进展, 其中主要介绍了三种该类化合物的手性合成方法, 即化学拆分、动力学拆分及通过手性金属配合物或有机小分子参与的不对称催化, 并对该领域未来的发展进行了展望.

关键词: 2-芳基-2H-色烯, 手性合成, 手性金属配合物催化, 有机小分子催化, 研究进展

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

引用此文

周顺丽, 刘继, 雷婷, 杨斌全, 江世智. 2-芳基-2H-色烯类化合物的手性合成研究进展[J]. 有机化学, 2026, 46(3): 773-785.

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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图/表 25

图式1. 刘兆鹏课题组的(S)-(＋)-α-甲氧基苯基乙酸化学拆分策略

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

图式2. Doris课题组的以Sharpless不对称环氧化为关键反应的策略

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

图式3. Park课题组的手性苄胺类配体催化脱水策略

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

图式4. 谢建武课题组的手性硫脲类双功能有机催化剂的动力学拆分策略

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

图式5. Park课题组的手性β-氨基醇类催化的不对称加成动力学拆分策略

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

图式6. Maji课题组的N-杂环卡宾(NHC)催化迈克尔加成策略

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

图式7. 汪君课题组的手性金属铑配合物催化的不对称氢芳基化策略

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

图式8. 侯国华课题组的铑催化不对称氢化动力学拆分策略

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

图式9. Scheidt课题组的[(salen)Cr(SbF6)]复合物催化不对称加成策略

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

图式10. 游书力课题组的铱催化分子间不对称烯丙基化策略

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

图式11. Scheidt 课题组的利钯催化分子内不对称烯丙基化策略

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

图式12. 候雪龙课题组的不对称Redox-Relay Heck反应策略

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

图式13. 王伟课题组的手性脯氨醇衍生物催化一锅法oxa-Michael-Aldol反应策略

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

图式14. 徐振元课题组的脯氨醇类手性仲胺催化oxa-Michael-Henry反应策略

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

图式15. 许丹倩课题组的联合催化剂催化oxa-Michael-Aldol反应策略

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

图式16. Schaus课题组的手性Brønsted酸与手性Lewis酸协同催化不对称加成策略

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

图式17. 徐利文课题组的手性二芳基脯氨醇硅醚催化oxa-Michael-Aldol反应策略

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

图式18. Schreiner课题组的双功能手性硫脲催化oxa-Michael-aza-Henry-desulfonmidation串联反应策略

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

图式19. Rueping课题组的手性有机接触离子对催化不对称烯丙基取代反应策略

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

图式20. 陈立功课题组的4-羟基脯氨酰胺催化oxa-Michael-Henry反应策略

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

图式21. Jacobsen课题组的手性方酰胺催化不对称硒环化及分子内开环相关策略

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

图式22. Denmark课题组的手性磷酰胺催化不对称硫酰碳正离子及分子内开环相关策略

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

图式23. Mohanta课题组的简单手性脯氨酰胺类小分子催化oxa-Michael-Henry反应策略

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

图式24. Agarwal课题组的手性L-脯氨酰胺催化水相oxa-Michael-Henry反应策略

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

图式25. 李崇龙课题组的环己二胺类手性小分子催化oxa-Michael-Aldol反应策略

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

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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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