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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

Unnatural α-amino ethyl esters from diethyl malonate or ethyl β-bromo-α-hydroxyiminocarboxylate

Scientific Fields
Diseases
Organisms
Applications
Technique

Published in Beilstein journal of organic chemistry - 16 Nov 2018

Coutant EP, Hervin V, Gagnot G, Ford C, Baatallah R, Janin YL

Link to Pubmed [PMID] – 30498536

Beilstein J Org Chem 2018;14:2853-2860

We have explored here the scope of the age-old diethyl malonate-based accesses to α-amino esters involving Knoevenagel condensations of diethyl malonate on aldehydes, reductions of the resulting alkylidenemalonates, the preparation of the corresponding α-hydroxyimino esters and their final reduction. This synthetic pathway turned out to be general although some unexpected limitations were encountered. The synthetic modifications of some of the intermediates – using Suzuki-Miyaura coupling or cycloadditions – before undertaking the oximation step – provided accesses to further α-amino esters. Moreover, other pathways to α-hydroxyimino esters were explored including an attempt to improve the cycloadditions between ethyl β-bromo-α-hydroxyiminocarboxylate and various alkylfuranes.

https://www.ncbi.nlm.nih.gov/pubmed/30498536