Issue 39, 2013
From the journal:

Chemical Communications

Enantioselective trapping of phosphoramidate ammonium ylides with iminoesters for synthesis of 2,3-diaminosuccinic acid derivatives†‡

Jun Jiang,a   Xiaochu Ma,a   Shunying Liu,a   Yu Qian,a   Fengping Lv,a   Lin Qiu,a   Xiang Wua  and  Wenhao Hu*a  

* Corresponding authors

a Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, East China Normal University, 3663 North Zhongshan Rd., Shanghai, China
E-mail: whu@chem.ecnu.edu.cn
Tel: +86-21-62221235

Abstract

A highly enantioselective trapping of protic phosphoramidate ammonium ylides with α-imino esters is reported. The intriguing Rh2(OAc)4 and chiral Brønsted acid co-catalyzed three-component Mannich-type reaction of a diazo compound, a phosphoramidate, and an α-imino ester provides a rapid and efficient access to 2,3-diaminosuccinic acid derivatives with a high level control of diastereo- and enantioselectivity.

Graphical abstract: Enantioselective trapping of phosphoramidate ammonium ylides with imino esters for synthesis of 2,3-diaminosuccinic acid derivatives

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Article information

DOI
https://doi.org/10.1039/C3CC36972B
Article type
Communication
Submitted
26 Sep 2012
Accepted
24 Dec 2012
First published
18 Jan 2013

Chem. Commun., 2013,49, 4238-4240

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Enantioselective trapping of phosphoramidate ammonium ylides with imino esters for synthesis of 2,3-diaminosuccinic acid derivatives

J. Jiang, X. Ma, S. Liu, Y. Qian, F. Lv, L. Qiu, X. Wu and W. Hu, Chem. Commun., 2013, 49, 4238 DOI: 10.1039/C3CC36972B

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