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Synthesis of Chiral α,β-Unsaturated γ-Amino Esters via Pd-Catalyzed Asymmetric Allylic Amination

Chao Xia, Jiefeng Shen, Delong Liu* and Wanbin Zhang*

*School of Pharmacy and School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai 200240, P. R. China, Email: dlliusjtu.edu.cn, wanbinsjtu.edu.cn

C. Xia, J. Shen, D. Liu, W. Zhang, Org. Lett., 2017, 19, 4251-4254.

DOI: 10.1021/acs.orglett.7b01904



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Abstract

A Pd-catalyzed asymmetric allylic amination of 4-substituted 2-acetoxybut-3-enoates with amines provides chiral α,β-unsaturated γ-amino esters in good yield and high ee. The products can be conveniently transformed to chiral γ-amino acid/alcohol derivatives and chiral γ-lactams.


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Key Words

allylic amination


ID: J54-Y2017