Issue 18, 2013
From the journal:

RSC Advances

Facile and efficient N-arylation of amino acid esters with (−)-methyl-3-dehydroshikimiate(3-MDHS): a bio-based and metal-free strategy leading to N-aryl amino acid derivatives†

Yong Zou,*ac   Ensheng Zhang,ab   Tianlong Xu,ab   Wei Wu,ab   Yu Chen,a   Mu Yuan,c   Wen Weia  and  Xuejing Zhangd  

* Corresponding authors

a Guangzhou Institute of Chemistry, Chinese Academy of Sciences, Guangzhou, P. R. of China
E-mail: zou_jinan@163.com
Fax: +86(20)85231119
Tel: +86(20)85231309

b University of Chinese Academy of Sciences, Beijing, P. R. of China

c Guangzhou Medical University, Guangzhou, P. R. of China
E-mail: mryuanmu@yahoo.com.cn

d Sun Yat-sen University, Guangzhou, P. R. of China
E-mail: zhangxj33@mail.sysu.edu.cn

Abstract

A novel and convenient bio-based protocol for the preparation of N-aryl amino acid derivatives from (−)-methyl-3-dehydroshikimate and amino acid esters via tandem cross-coupling and aromatization reactions has been developed. Various N-aryl amino acid esters were synthesized in moderate to high yields under mild and metal-free conditions without using aryl halides.

Graphical abstract: Facile and efficient N-arylation of amino acid esters with (−)-methyl-3-dehydroshikimiate(3-MDHS): a bio-based and metal-free strategy leading to N-aryl amino acid derivatives

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Article information

DOI
https://doi.org/10.1039/C3RA40650D
Article type
Paper
Submitted
15 Dec 2012
Accepted
19 Feb 2013
First published
20 Feb 2013

RSC Adv., 2013,3, 6545-6552

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Facile and efficient N-arylation of amino acid esters with (−)-methyl-3-dehydroshikimiate(3-MDHS): a bio-based and metal-free strategy leading to N-aryl amino acid derivatives

Y. Zou, E. Zhang, T. Xu, W. Wu, Y. Chen, M. Yuan, W. Wei and X. Zhang, RSC Adv., 2013, 3, 6545 DOI: 10.1039/C3RA40650D

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