Issue 39, 2013

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

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

Supplementary files

Article information

Article type
Communication
Submitted
26 Sep 2012
Accepted
24 Des 2012
First published
18 Jan 2013

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

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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