Synlett 2017; 28(04): 485-488
DOI: 10.1055/s-0036-1588096
letter
© Georg Thieme Verlag Stuttgart · New York

Dehydrogenative Cross-Coupling Reactions of N-Aryl α-Amino Acid Esters with Nitroalkanes for the Synthesis of β-Nitro α-Amino Acid Esters

Zhi-Qiang Zhu*
a   Jiangxi 2011 Joint Center for Innovative Mass Spectrometry and Instrumentation, East China University of Technology, Nanchang 330013, P. R. of China
b   School of Chemistry, Biology and Material Science, East China University of Technology, Nanchang 330013, P. R. of China   Email: zhuzq@ecit.cn   Email: zhgle@ecit.cn
,
Zong-Bo Xie
a   Jiangxi 2011 Joint Center for Innovative Mass Spectrometry and Instrumentation, East China University of Technology, Nanchang 330013, P. R. of China
b   School of Chemistry, Biology and Material Science, East China University of Technology, Nanchang 330013, P. R. of China   Email: zhuzq@ecit.cn   Email: zhgle@ecit.cn
,
Zhang-Gao Le*
a   Jiangxi 2011 Joint Center for Innovative Mass Spectrometry and Instrumentation, East China University of Technology, Nanchang 330013, P. R. of China
b   School of Chemistry, Biology and Material Science, East China University of Technology, Nanchang 330013, P. R. of China   Email: zhuzq@ecit.cn   Email: zhgle@ecit.cn
› Author Affiliations
Further Information

Publication History

Received: 22 August 2016

Accepted after revision: 21 October 2016

Publication Date:
10 November 2016 (online)


Abstract

A novel copper-catalyzed dehydrogenative cross-coupling reaction of N-aryl α-amino acid esters with nitroalkanes to give β-nitro α-amino acid esters was developed. Various N-aryl α-amino acid esters reacted smoothly with nitroalkanes to give the desired coupling products in moderate to good yields. The method uses a cheap and simple copper salt as a catalyst and molecular oxygen as an environmentally benign oxidant. A possible mechanism for the dehydrogenative cross-coupling reaction is proposed.

Supporting Information