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

Xuezhen Kou; Yongjin Xu; Siqi Dong; Hui Liu; Delong Liu; Wanbin Zhang

doi:10.1055/s-0044-1788722

Pharmaceutical Fronts, Table of Contents

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

Authors

Xuezhen Kou^#

¹Frontier Science Center for Transformative Molecules, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai, People's Republic of China
Yongjin Xu^#

²State Key Laboratory of Coking Coal Exploitation and Comprehensive Utilization, Pingdingshan, People's Republic of China
Siqi Dong

³Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, School of Pharmacy, Shanghai Jiao Tong University, Shanghai, People's Republic of China
Hui Liu

²State Key Laboratory of Coking Coal Exploitation and Comprehensive Utilization, Pingdingshan, People's Republic of China
Delong Liu

³Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, School of Pharmacy, Shanghai Jiao Tong University, Shanghai, People's Republic of China
Wanbin Zhang

¹Frontier Science Center for Transformative Molecules, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai, People's Republic of China

³Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, School of Pharmacy, Shanghai Jiao Tong University, Shanghai, People's Republic of China

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

Full Text

References

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