Issue 19, 2017
From the journal:

Chemical Communications

Iron catalyzed efficient synthesis of poly-functional primary amines via the direct use of ammonia†

Chaoqun Ma,a   Jianghui Chen,a   Dong Xing,a   Yuan Shenga  and  Wenhao Hu ORCID logo *a  

* Corresponding authors

a Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, School of Chemistry and Molecular Engineering East China Normal University, 3663 North Zhongshan Rd., Shanghai 200062, China
E-mail: whu@chem.ecnu.edu.cn

Abstract

An iron catalyzed three-component reaction of alkyl diazoesters, isatins and ammonia is reported. This reaction provided convenient access to non-protected β-hydroxy-α-aminoesters with adjacent quaternary stereocenters. This transformation is achieved via trapping of ammonium ylide which is generated from a diazocompound and ammonia under mild reaction conditions. Poly-functional group unprotected amines are obtained exclusively with up to 77% yield and 62 : 38 dr.

Graphical abstract: Iron catalyzed efficient synthesis of poly-functional primary amines via the direct use of ammonia

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Article information

DOI
https://doi.org/10.1039/C7CC00003K
Article type
Communication
Submitted
01 Jan 2017
Accepted
13 Feb 2017
First published
13 Feb 2017

Chem. Commun., 2017,53, 2854-2857

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Iron catalyzed efficient synthesis of poly-functional primary amines via the direct use of ammonia

C. Ma, J. Chen, D. Xing, Y. Sheng and W. Hu, Chem. Commun., 2017, 53, 2854 DOI: 10.1039/C7CC00003K

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