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Issue 39, 2013
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Enantioselective trapping of phosphoramidate ammonium ylides with imino esters for synthesis of 2,3-diaminosuccinic acid derivatives

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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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Publication details

The article was received on 26 Sep 2012, accepted on 24 Dec 2012 and first published on 18 Jan 2013


Article type: Communication
DOI: 10.1039/C3CC36972B
Citation: 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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