Construction of Quaternary Allylic Amino Acid Derivatives through Palladium-Catalyzed Allylic Alkylation Reaction of Azlactones with Vinyl Aziridine

Ke-Xin Huang; Zhao-Yang Chen; Xue-Guo Liu; Hong-Yong Ye; Wen-Chao Gao

doi:10.1055/a-1878-8084

Synthesis, Table of Contents

Synthesis 2022; 54(20): 4495-4502
DOI: 10.1055/a-1878-8084

paper

Construction of Quaternary Allylic Amino Acid Derivatives through Palladium-Catalyzed Allylic Alkylation Reaction of Azlactones with Vinyl Aziridine

Ke-Xin Huang ∗

^aSchool of Biological and Chemical Engineering, Nanyang Institute of Technology, Nanyang, Henan 473000, P. R. of China

,

Zhao-Yang Chen

^aSchool of Biological and Chemical Engineering, Nanyang Institute of Technology, Nanyang, Henan 473000, P. R. of China

,

Xue-Guo Liu

^aSchool of Biological and Chemical Engineering, Nanyang Institute of Technology, Nanyang, Henan 473000, P. R. of China

,

Hong-Yong Ye

^aSchool of Biological and Chemical Engineering, Nanyang Institute of Technology, Nanyang, Henan 473000, P. R. of China

,

Wen-Chao Gao∗

^bSchool of Chemistry and Pharmaceutical Engineering, Nanyang Normal University, Nanyang, Henan 473000, P. R. of China

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Abstract

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Abstract

A highly efficient Pd-catalyzed allylic alkylation reaction of azlactones with vinyl aziridine has been achieved for the first time to access functionalized quaternary allylic amino acid derivatives (17 examples, up to 89% yield and 80% ee). Moreover, the broad scope and easy transformations of the products reinforce the value of this approach, which can enrich the chemistry of quaternary allylic amino acid derivatives.

Key words

allylic alkylation - quaternary allylic amino acid derivatives - Pd-catalyzed - vinyl aziridine - azlactones

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References

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