Chiral Bicyclo[2.2.2]octane-Fused and Ferrocene-Derived Cyclopentadienyl Ligands for Asymmetric C–H Activation

Hao Liang; Jun Wang

doi:10.1055/a-1992-6757

Synlett, Table of Contents

Synlett 2023; 34(08): 882-888
DOI: 10.1055/a-1992-6757

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Chiral Bicyclo[2.2.2]octane-Fused and Ferrocene-Derived Cyclopentadienyl Ligands for Asymmetric C–H Activation

Hao Liang

^aKey Laboratory of Bioinorganic and Synthetic Chemistry of Ministry of Education, School of Chemistry, Sun Yat-Sen University, Guangzhou, 510006, P. R. China

^bGuangdong Key Laboratory of Chiral Molecule and Drug Discovery, Sun Yat-Sen University, Guangzhou, 510006, P. R. China

,

Jun Wang∗

^aKey Laboratory of Bioinorganic and Synthetic Chemistry of Ministry of Education, School of Chemistry, Sun Yat-Sen University, Guangzhou, 510006, P. R. China

^bGuangdong Key Laboratory of Chiral Molecule and Drug Discovery, Sun Yat-Sen University, Guangzhou, 510006, P. R. China

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Abstract

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Abstract

To fulfill increasing and diverse demands of cyclopentadienyl metal complexes (CpM) catalyzed asymmetric C–H activation, innovation in developing new types of chiral Cp ligands should be important. In this context, we found the structurally rigid chiral bicyclo[2.2.2]octane-fused Cp ligands originated by Vollhardt and Halterman were efficient to enable highly enantioselective C–H activation of N-methoxybenzamides with quinones. Besides, we also designed and synthesized a class of ferrocene-based chiral Cp ligand featuring a loose chiral pocket, whose rhodium complexes exhibited high reactivity and reasonable enantioselectivity in an asymmetric intramolecular aryl amination of alkene.

1 Introduction

2 Chiral Cp Ligands Applied in Asymmetric C–H Activation

3 Chiral Bicyclo[2.2.2]octane-Fused Cp Ligands

4 Chiral Ferrocene-Derived Cp Ligands

5 Conclusion

Key words

chiral cyclopentadienyl - bicyclo[2.2.2]octane - ferrocene - rhodium - asymmetric C–H activation

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