Advances in the Intermolecular Asymmetric Allylic Functionalization of Unreactive Acyclic Alkenes

Mingyue Zhang; Mengmeng Zhang; Changsheng Li; Wenyang Wang; Guohui Shi; Shipeng Luo; Liang-An Chen; Qiang Dai

doi:10.1055/a-2375-7634

Synlett, Table of Contents

Synlett 2025; 36(04): 311-321
DOI: 10.1055/a-2375-7634

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Thieme Chemistry Journals Awardees 2024

Advances in the Intermolecular Asymmetric Allylic Functionalization of Unreactive Acyclic Alkenes

Mingyue Zhang

^aJiangsu Collaborative Innovation Center of Biomedical Functional Materials, Jiangsu Key Laboratory of New Power Batteries, School of Chemistry and Materials Science, Nanjing Normal University, Nanjing 210023, P. R. of China

,

Mengmeng Zhang

^aJiangsu Collaborative Innovation Center of Biomedical Functional Materials, Jiangsu Key Laboratory of New Power Batteries, School of Chemistry and Materials Science, Nanjing Normal University, Nanjing 210023, P. R. of China

,

Changsheng Li

^aJiangsu Collaborative Innovation Center of Biomedical Functional Materials, Jiangsu Key Laboratory of New Power Batteries, School of Chemistry and Materials Science, Nanjing Normal University, Nanjing 210023, P. R. of China

,

Wenyang Wang

^aJiangsu Collaborative Innovation Center of Biomedical Functional Materials, Jiangsu Key Laboratory of New Power Batteries, School of Chemistry and Materials Science, Nanjing Normal University, Nanjing 210023, P. R. of China

,

Guohui Shi

^aJiangsu Collaborative Innovation Center of Biomedical Functional Materials, Jiangsu Key Laboratory of New Power Batteries, School of Chemistry and Materials Science, Nanjing Normal University, Nanjing 210023, P. R. of China

,

Shipeng Luo

^bSchool of Chemistry and Chemical Engineering, Jiangsu University of Technology, Changzhou 213001, P. R. of China

,

Liang-An Chen ∗

^aJiangsu Collaborative Innovation Center of Biomedical Functional Materials, Jiangsu Key Laboratory of New Power Batteries, School of Chemistry and Materials Science, Nanjing Normal University, Nanjing 210023, P. R. of China

,

Qiang Dai ∗

^aJiangsu Collaborative Innovation Center of Biomedical Functional Materials, Jiangsu Key Laboratory of New Power Batteries, School of Chemistry and Materials Science, Nanjing Normal University, Nanjing 210023, P. R. of China

› Author Affiliations

Abstract

All articles of this category

Abstract

Allylic C(sp ³)–H functionalized architectures are not only widely present in natural products, pharmaceuticals, and functional organic materials, but also serve as versatile building blocks to furnish important functionalized molecules in synthetic chemistry. Accordingly, various strategies to access allylic functionalized alkenes in a stereoselective manner have been developed. However, chemo-, regio- and stereoselective intermolecular asymmetric allylic functionalization (AAF) of unreactive acyclic alkene (UAA) from readily available materials, representing a highly atom- and step-economic approach toward the generation of structural complexity, remains elusive and challenging. Herein, we review all intermolecular asymmetric catalyzed methods, with emphasis on the construction of chiral allylic units by activation of allylic C–H bonds of UAAs. Our analysis serves to document the considerable and rapid progress within the field, while also highlighting the limitations of current methods.

1 Introduction

2 Asymmetric Allylic Oxygenation

3 Asymmetric Allylic Amination

4 Asymmetric Allylic Carbonization

5 Asymmetric Allylic Sulfuration

6 Conclusion and Outlook

Key words

asymmetric - allylic functionalization - unreactive acyclic alkene - C–H activation - selectivity

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References

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