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© Institut Pasteur
Cristaux de cellulase, enzyme purifiée de Clostridium thermocellum permettant la digestion de la cellulose. Image colorisée.
Publication : Beilstein journal of organic chemistry

Synthesis of unnatural α-amino esters using ethyl nitroacetate and condensation or cycloaddition reactions

Scientific Fields
Diseases
Organisms
Applications
Technique

Published in Beilstein journal of organic chemistry - 15 Nov 2018

Gagnot G, Hervin V, Coutant EP, Desmons S, Baatallah R, Monnot V, Janin YL

Link to Pubmed [PMID] – 30498535

Beilstein J Org Chem 2018;14:2846-2852

We report here on the use of ethyl nitroacetate as a glycine template to produce α-amino esters. This started with a study of its condensation with various arylacetals to give ethyl 3-aryl-2-nitroacrylates followed by a reduction (NaBH and then zinc/HCl) into α-amino esters. The scope of this method was explored as well as an alternative with arylacylals instead. We also focused on various [2 + 3] cycloadditions, one leading to a spiroacetal, which led to the undesired ethyl 5-(benzamidomethyl)isoxazole-3-carboxylate. The addition of ethyl nitroacetate on a 5-methylene-4,5-dihydrooxazole using cerium(IV) ammonium nitrate was also explored and the synthesis of other oxazole-bearing α-amino esters was achieved using gold(I) chemistry.

https://www.ncbi.nlm.nih.gov/pubmed/30498535