三氟乙基酮亚胺参与的催化不对称反应研究进展

doi:10.6023/cjoc202011005

有机化学 ›› 2021, Vol. 41 ›› Issue (5): 1789-1803.DOI: 10.6023/cjoc202011005 上一篇下一篇

综述与进展

三氟乙基酮亚胺参与的催化不对称反应研究进展

孙忠文¹^,^*(), 张聪聪¹, 陈丽君¹, 谢惠定¹, 柳波¹, 刘丹丹¹^,^*()

1 昆明医科大学药学院云南省天然药物药理重点实验室昆明 650500

收稿日期:2020-11-04 修回日期:2020-12-10 发布日期:2020-12-31
通讯作者: 孙忠文, 刘丹丹
基金资助:
国家自然科学基金(21907044); 云南省基础研究计划项目(2019FB124); 云南省科技厅-昆明医科大学应用基础研究联合专项基金项目(2017FE468(-138)); 云南省教育厅科学研究基金(2016ZZX089); 西南林业大学西南地区林业生物质高效利用国家林和草原局重点实验室开放基金(2019-KF18); 西南林业大学西南地区林业生物质高效利用国家林和草原局重点实验室开放基金(2020-KF06)

Recent Advances in Catalytic Asymmetric Reactions Involving Trifluoroethyl Ketimines

Zhongwen Sun¹^,^*(), Congcong Zhang¹, Lijun Chen¹, Huiding Xie¹, Bo Liu¹, Dandan Liu¹^,^*()

1 School of Pharmaceutical Science & Yunnan Key Laboratory of Pharmacology for Natural Products, Kunming Medical University, Kunming 650500

Received:2020-11-04 Revised:2020-12-10 Published:2020-12-31
Contact: Zhongwen Sun, Dandan Liu
About author:
* Corresponding authors. E-mail: 527301858@qq.com;
E-mail: liudandan1017@qq.com
Supported by:
National Natural Science Foundation of China(21907044); Yunnan Fundamental Research Projects(2019FB124); Yunnan Provincial Science and Technology Department-Kunming Medical University Applied Basic Research Joint Special Fund Project(2017FE468(-138)); Yunnan Provincial Department of Education Science Research Fund Project(2016ZZX089); Open Fund of Key Laboratory of State Forestry and Grassland Adminstration on Highly-Efficient Utilization of Forestry Biomass Resources in Southwest China, Southwest Forestry University(2019-KF18); Open Fund of Key Laboratory of State Forestry and Grassland Adminstration on Highly-Efficient Utilization of Forestry Biomass Resources in Southwest China, Southwest Forestry University(2020-KF06)

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摘要/Abstract

氟原子或含氟基团在材料科学、药物化学等领域的生物活性分子中广泛存在. 三氟乙基酮亚胺同时存在高活性亲电和亲核中心, 是良好的1,3-偶极子. 因其在催化不对称构建含有三氟甲基立体中心的反应中具有极高的研究价值而备受关注. 以三氟乙基酮亚胺的底物和反应类型为主线, 综述了近五年三氟乙基酮亚胺参与的催化不对称反应研究进展, 同时对该领域的未来发展进行了展望.

关键词: 三氟乙基酮亚胺, 不对称催化, 环加成反应, 三氟甲基, 手性胺合成

The fluorine atoms or fluorine-containing groups are widely found in biologically molecules in the fields of materials science, pharmaceutical chemistry, etc. The properties of trifluoroethylketimines provide both electrophilic and nucleophilic centers, and become an excellent 1,3-dipole, which possessed high research value in catalytic asymmetric reactions of construction of trifluoromethyl stereocenters. Based on the substrates and reaction types of trifluoroethylketimine, the research progress of catalytic asymmetric reactions involving trifluoroethylketimine in recent five years is reviewed, and the future development of this field is prospected.

Key words: trifluoroethylketimine, asymmetric catalysis, cycloaddition, trifluoromethyl group, synthesis of chiral amine

引用此文

孙忠文, 张聪聪, 陈丽君, 谢惠定, 柳波, 刘丹丹. 三氟乙基酮亚胺参与的催化不对称反应研究进展[J]. 有机化学, 2021, 41(5): 1789-1803.

Zhongwen Sun, Congcong Zhang, Lijun Chen, Huiding Xie, Bo Liu, Dandan Liu. Recent Advances in Catalytic Asymmetric Reactions Involving Trifluoroethyl Ketimines[J]. Chinese Journal of Organic Chemistry, 2021, 41(5): 1789-1803.

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图/表 24

图1. 含三氟甲基手性中心的生物活性分子

Figure 1. Selected biologically active molecules bearing a CF3 chiral center

图式1. 常见三氟乙基酮亚胺的类型及反应

Scheme 1. Types and reactions of common trifluoroethylketimines

图式2. 催化三氟乙基吲哚酮亚胺与烯醛不对称[3+2]环加成反应

Scheme 2. Catalytic asymmetric [3+2] cycloaddition of trifluoroethylisatin ketimines and enals

图式3. 有机催化硝基烯与三氟乙基吲哚酮亚胺不对称环加成反应

Scheme 3. Organocatalytic asymmetric cycloaddition of nitroalkenes with trifluoroethylisatin ketimines

图式4. 三氟乙基吲哚酮亚胺与β-三氟甲基烯酮的不对称环加成反应

Scheme 4. Asymmetric cycloaddition of trifluoroethylisatin ketimines and β-trifluoromethylenones

图式5. 乙烯基取代芳醛与三氟乙基吲哚酮亚胺不对称环加成反应

Scheme 5. Asymmetric cycloaddition of trifluoroethylisatin ketimines with vinyl substituted aryl aldehydes

图式6. 环状2,4-二烯酮与三氟乙基吲哚酮亚胺的远程区域选择性的不对称环加成反应

Scheme 6. Remote regioselective asymmetric cycloaddition of trifluoroethylisatin ketimines with cyclic 2,4-dienones

. 图示7 三氟乙基吲哚酮亚胺与3-烯基-5-芳基呋喃2(3H)-酮的不对称[3+2]环加成反应

Scheme 7. Asymmetric [3+2] cycloaddition of 3-alkenyl-5- arylfuran-2(3H)-ones with trifluoroethylisatin ketimines

图式8. 杜大明课题组关于环外烯烃与三氟乙基吲哚酮亚胺不对称环加成反应的研究

Scheme 8. Asymmetric cycloaddition of exocyclic olefins with trifluoroethylisatin ketimines by Du's group

图式9. 有机催化橙酮和α,β-不饱和吡唑啉酮与吲哚酮亚胺的不对称环加成反应

Scheme 9. Organocatalytic asymmetric cycloaddition between isatinketimines and aurones & α,β-unsaturated pyrazolones

图式10. 2,3-二羰基吡咯烷非对映选择性发散的不对称[3+2]环加成反应

Scheme 10. Diastereodivergent asymmetric [3+2] cycloaddition of 2,3-dioxopyrrolidines

图式11. 手性双功能季磷盐催化的不对称1,3-偶极环加成反应

Scheme 11. Asymmetric 1,3-dipolar cycloaddition via chiral bifunctionalphosphonium salt

图式12. 吲哚酮亚胺与3-甲烯基吲哚酮催化不对称环加成反应

Scheme 12. Catalytic asymmetric cycloaddition of isatin-based ketamines with 3-metheneindolinones

图式13. 有机催化3-三氟亚乙基吲哚酮与吲哚酮亚胺之间的不对称环加成反应

Scheme 13. Organocatalytic asymmetric cycloaddition of isatin-based ketamines with 3-trifluoroethylideneoxindoles

图式14. MBH型碳酸酯与吲哚酮亚胺之间的催化不对称SN2'-SN2'反应

Scheme 14. Catalyzed asymmetric SN2'-SN2' reaction between MBH type carbonates and isatin-based ketamines

图式15. 三氟乙基吲哚酮亚胺的催化不对称极性反转烯丙基化/2-氮杂-Cope重排串联反应

Scheme 15. Catalytic asymmetric cascade umpolung allylation/2-aza-Cope rearrangement reactions of isatin-based ketamines

图式16. 末端二烯与吲哚酮亚胺的催化不对称加氢烷基化反应

Scheme 16. Catalytic asymmetric hydroalkylation of terminadiene with isatin-based ketamines

图式17. 催化三氟乙基吲哚酮亚胺的不对称极性反转交叉Mannich反应

Scheme 17. Catalytic asymmetric umpolung cross-Mannich reaction of trifluoroethylisatin ketimines

图式18. 手性铱催化三氟乙基吲哚酮亚胺的不对称极性反转烯丙基化/2-氮杂-Cope重排串联反应

Scheme 18. Chiral iridium catalyzed asymmetric cascade umpolung allylation/2-aza-Cope rearrangement reactions of isatin-based ketamines

图式19. 钯催化三氟乙基芴基酮亚胺的不对称烯丙基化反应

Scheme 19. Palladium-catalyzed asymmetric allylation of trifluoroethylfluorene ketimines

图式20. 催化酮亚胺极性反转的不对称[3+2]环加成反应

Scheme 20. Catalytic asymmetric umpolung and [3+2] cycloaddition of ketimines

图式21. 有机催化三氟乙基酮亚胺不对称环加成反应构建手性吡咯烷

Scheme 21. Asymmetric construction of chiral pyrrolidines via organocatalytic cycloaddition of trifluoroethylfluorene ketimines

图式22. 催化不对称[3+2]环加成反应构建手性螺环吡咯烷-噻唑酮化合物

Scheme 22. Construction of chiral spiro-thiazolone-pyrrolidine compounds via catalytic asymmetric [3+2] cycloaddition

图式23. 有机催化酮亚胺与羰基化合物的不对称1,3-偶极环加成反应

Scheme 23. Organocatalytic asymmetric 1,3-dopolar cycloaddition of ketimines with carbonyl compounds

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三氟乙基酮亚胺参与的催化不对称反应研究进展

Recent Advances in Catalytic Asymmetric Reactions Involving Trifluoroethyl Ketimines

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