Unnatural α-amino ethyl esters from diethyl malonate or ethyl β-bromo-α-hydroxyiminocarboxylate - Archive ouverte HAL Access content directly
Journal Articles Beilstein Journal of Organic Chemistry Year : 2018

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

Abstract

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.
Fichier principal
Vignette du fichier
1860-5397-14-264.pdf (429.95 Ko) Télécharger le fichier
Loading...

Dates and versions

pasteur-01972143 , version 1 (07-01-2019)

Licence

Attribution - CC BY 4.0

Identifiers

Cite

Eloi Coutant, Vincent Hervin, Glwadys Gagnot, Candice Ford, Racha Baatallah, et al.. Unnatural α-amino ethyl esters from diethyl malonate or ethyl β-bromo-α-hydroxyiminocarboxylate. Beilstein Journal of Organic Chemistry, 2018, 14, pp.2853-2860. ⟨10.3762/bjoc.14.264⟩. ⟨pasteur-01972143⟩
24 View
357 Download

Altmetric

Share

Gmail Facebook Twitter LinkedIn More