Issue 45, 2016

In situ generation of nitrilium from nitrile ylide and the subsequent Mumm rearrangement: copper-catalyzed synthesis of unsymmetrical diacylglycine esters

Abstract

A novel in situ generation of nitrilium from a nitrile ylide and the subsequent Mumm rearrangement of carboxylic acid, nitrile, and diazo compounds gave various unsymmetrical diacylglycine esters in moderate to high yields. This copper-catalyzed cascade reaction enables one-pot generation of two C–N bonds, one C[double bond, length as m-dash]O bond, and one C–H bond, with nitrogen as the only byproduct. The reaction has a broad functional-group tolerance, is rapid, easily scales up to the 100 mmol scale, and is insensitive to air and moisture.

Graphical abstract: In situ generation of nitrilium from nitrile ylide and the subsequent Mumm rearrangement: copper-catalyzed synthesis of unsymmetrical diacylglycine esters

Supplementary files

Article information

Article type
Paper
Submitted
17 Sep 2016
Accepted
27 Oct 2016
First published
27 Oct 2016

Org. Biomol. Chem., 2016,14, 10723-10732

In situ generation of nitrilium from nitrile ylide and the subsequent Mumm rearrangement: copper-catalyzed synthesis of unsymmetrical diacylglycine esters

J. Chen, Y. Shao, L. Ma, M. Ma and X. Wan, Org. Biomol. Chem., 2016, 14, 10723 DOI: 10.1039/C6OB02037B

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