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CC BY 4.0 · Pharmaceutical Fronts 2024; 06(03): e237-e251
DOI: 10.1055/s-0044-1788722
Review Article

Pd-Catalyzed Asymmetric Allylic Substitution Cascade via Desymmetrization for the Construction of Chiral Polyheterocycles

Xuezhen Kou   #
1   Frontier Science Center for Transformative Molecules, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai, People's Republic of China
,
Yongjin Xu   #
2   State Key Laboratory of Coking Coal Exploitation and Comprehensive Utilization, Pingdingshan, People's Republic of China
,
Siqi Dong
3   Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, School of Pharmacy, Shanghai Jiao Tong University, Shanghai, People's Republic of China
,
Hui Liu
2   State Key Laboratory of Coking Coal Exploitation and Comprehensive Utilization, Pingdingshan, People's Republic of China
,
Delong Liu
3   Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, School of Pharmacy, Shanghai Jiao Tong University, Shanghai, People's Republic of China
,
Wanbin Zhang
1   Frontier Science Center for Transformative Molecules, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai, People's Republic of China
3   Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, School of Pharmacy, Shanghai Jiao Tong University, Shanghai, People's Republic of China
› Author Affiliations Funding This work was supported by the National Key R&D Program of China (Grant No. 2023YFA1506700) and the National Natural Science Foundation of China (Grant Nos. 2271185 and 21620102003). The authors also thank the Instrumental Analysis Center of Shanghai Jiao Tong University for its characterization.
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Abstract

Chiral polyheterocycles represent an important class of compounds because of their prevalence in bioactive natural products and chiral drugs. Pd-catalyzed allylic substitution is a powerful synthetic tool for forming C–C and C–X bonds (X = N, O, S, etc.). Naturally, asymmetric cascade reactions that utilize allylic substitution are undoubtedly efficient pathways to construct heterocycles. In this article, we reviewed the Pd-catalyzed asymmetric allylic substitution cascade via the desymmetrization of meso-diol diesters of cycloolefins, for the construction of chiral polyheterocycles and their derivatives.

Keywords

Pd-catalyst - asymmetric cascade allylic substitution - desymmetrization - chiral polyheterocycles - synthesis

# These authors contributed equally to this work.




Publication History

Received: 13 April 2024

Accepted: 15 July 2024

Article published online:
06 August 2024

© 2024. The Author(s). This is an open access article published by Thieme under the terms of the Creative Commons Attribution License, permitting unrestricted use, distribution, and reproduction so long as the original work is properly cited. (https://creativecommons.org/licenses/by/4.0/)

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