Issue 4, 2016

Synthesis of α-diazo-β-keto esters, phosphonates and sulfones via acylbenzotriazole-mediated acylation of a diazomethyl anion

Abstract

We report a method for the synthesis of α-diazo-β-keto esters, phosphonates and sulfones via acylation of corresponding diazomethyl anions with N-acylbenzotriazoles. The N-o-amino-acylbenzotriazoles exhibited an unprecedented transphosphorylation reaction leading to diazoacetyl phenylphosphoramidates.

Graphical abstract: Synthesis of α-diazo-β-keto esters, phosphonates and sulfones via acylbenzotriazole-mediated acylation of a diazomethyl anion

Supplementary files

Article information

Article type
Paper
Submitted
22 Sep 2015
Accepted
06 Oct 2015
First published
14 Oct 2015

Org. Biomol. Chem., 2016,14, 1239-1243

Author version available

Synthesis of α-diazo-β-keto esters, phosphonates and sulfones via acylbenzotriazole-mediated acylation of a diazomethyl anion

M. M. D. Pramanik and N. Rastogi, Org. Biomol. Chem., 2016, 14, 1239 DOI: 10.1039/C5OB01975C

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