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
a   School of Biological and Chemical Engineering, Nanyang Institute of Technology, Nanyang, Henan 473000, P. R. of China
,
Zhao-Yang Chen
a   School of Biological and Chemical Engineering, Nanyang Institute of Technology, Nanyang, Henan 473000, P. R. of China
,
Xue-Guo Liu
a   School of Biological and Chemical Engineering, Nanyang Institute of Technology, Nanyang, Henan 473000, P. R. of China
,
Hong-Yong Ye
a   School of Biological and Chemical Engineering, Nanyang Institute of Technology, Nanyang, Henan 473000, P. R. of China
,
Wen-Chao Gao
b   School of Chemistry and Pharmaceutical Engineering, Nanyang Normal University, Nanyang, Henan 473000, P. R. of China
› Author Affiliations
We are grateful for the financial support from Youth Foundation of Henan Scientific Committee (No. 222300420249), Foundation of Henan Education Committee (No. 21A150039) and Doctoral Research Start-up Fund project of Nanyang Institute of Technology (No. NGBJ-2021-03).


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.

Supporting Information



Publication History

Received: 15 April 2022

Accepted after revision: 20 June 2022

Accepted Manuscript online:
20 June 2022

Article published online:
27 July 2022

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