Recent Advances in Catalytic Asymmetric Reactions Involving Trifluoroethyl Ketimines

doi:10.6023/cjoc202011005

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (5): 1789-1803.DOI: 10.6023/cjoc202011005 Previous Articles Next Articles

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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

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)

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

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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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Fig. & Tab. 24

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

Scheme 1. Types and reactions of common trifluoroethylketimines

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

Scheme 3. Organocatalytic asymmetric cycloaddition of nitroalkenes with trifluoroethylisatin ketimines

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Scheme 19. Palladium-catalyzed asymmetric allylation of trifluoroethylfluorene ketimines

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

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

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

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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Fig. & Tab. 24

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