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Article

Diastereoselective Formal 1,3-Dipolar Cycloaddition of Trifluoroethyl Amine-Derived Ketimines Enables the Desymmetrization of Cyclopentenediones

by
Lin-Qiang Li
1,2,3,
Jian-Qiang Zhao
1,*,
Yan-Ping Zhang
1,
Yong You
1,
Zhen-Hua Wang
1,
Zhen-Zhen Ge
3,
Ming-Qiang Zhou
2,3 and
Wei-Cheng Yuan
1,2,*
1
Innovation Research Center of Chiral Drugs, Institute for Advanced Study, Chengdu University, Chengdu 610106, China
2
School of Pharmacy, Zunyi Medical University, Zunyi 563000, China
3
National Engineering Research Center of Chiral Drugs, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, China
*
Authors to whom correspondence should be addressed.
Molecules 2023, 28(14), 5372; https://doi.org/10.3390/molecules28145372
Submission received: 23 June 2023 / Revised: 7 July 2023 / Accepted: 11 July 2023 / Published: 13 July 2023
(This article belongs to the Special Issue Bioactive Heterocyclic Chemistry)
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Abstract

In this research, a metal-free diastereoselective formal 1,3-dipolar cycloaddition of N-2,2,2-trifluoroethylisatin ketimines and cyclopentene-1,3-diones which can efficiently lead to the desymmetrization of cyclopentene-1,3-diones is developed. With the developed protocol, a series of tetracyclic spirooxindoles containing pyrrolidine and cyclopentane subunits can be smoothly obtained with good results (up to 99% yield and 91:9 dr). Furthermore, the methodology can be extended to trifluoromethyl-substituted iminomalonate, and the corresponding formal [3+2] cycloaddition reaction affords bicyclic heterocycles containing fused pyrrolidine and cyclopentane moieties in moderate yields with >20:1 dr. The synthetic potential of the methodology is demonstrated by the scale-up experiment and by versatile transformations of the products.
Keywords: desymmetrization; 1,3-dipolar cycloaddition; cyclopentene-1,3-diones; trifluoroethyl amine-derived ketimines; polycyclic heterocycles desymmetrization; 1,3-dipolar cycloaddition; cyclopentene-1,3-diones; trifluoroethyl amine-derived ketimines; polycyclic heterocycles
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MDPI and ACS Style

Li, L.-Q.; Zhao, J.-Q.; Zhang, Y.-P.; You, Y.; Wang, Z.-H.; Ge, Z.-Z.; Zhou, M.-Q.; Yuan, W.-C. Diastereoselective Formal 1,3-Dipolar Cycloaddition of Trifluoroethyl Amine-Derived Ketimines Enables the Desymmetrization of Cyclopentenediones. Molecules 2023, 28, 5372. https://doi.org/10.3390/molecules28145372

AMA Style

Li L-Q, Zhao J-Q, Zhang Y-P, You Y, Wang Z-H, Ge Z-Z, Zhou M-Q, Yuan W-C. Diastereoselective Formal 1,3-Dipolar Cycloaddition of Trifluoroethyl Amine-Derived Ketimines Enables the Desymmetrization of Cyclopentenediones. Molecules. 2023; 28(14):5372. https://doi.org/10.3390/molecules28145372

Chicago/Turabian Style

Li, Lin-Qiang, Jian-Qiang Zhao, Yan-Ping Zhang, Yong You, Zhen-Hua Wang, Zhen-Zhen Ge, Ming-Qiang Zhou, and Wei-Cheng Yuan. 2023. "Diastereoselective Formal 1,3-Dipolar Cycloaddition of Trifluoroethyl Amine-Derived Ketimines Enables the Desymmetrization of Cyclopentenediones" Molecules 28, no. 14: 5372. https://doi.org/10.3390/molecules28145372

APA Style

Li, L.-Q., Zhao, J.-Q., Zhang, Y.-P., You, Y., Wang, Z.-H., Ge, Z.-Z., Zhou, M.-Q., & Yuan, W.-C. (2023). Diastereoselective Formal 1,3-Dipolar Cycloaddition of Trifluoroethyl Amine-Derived Ketimines Enables the Desymmetrization of Cyclopentenediones. Molecules, 28(14), 5372. https://doi.org/10.3390/molecules28145372

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