Unnatural α-amino ethyl esters from diethyl malonate or ethyl ß-bromo-α-hydroxyiminocarboxylate.
Beilstein J Org Chem
; 14: 2853-2860, 2018.
Article
em En
| MEDLINE
| ID: mdl-30498536
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 ß-bromo-α-hydroxyiminocarboxylate and various alkylfuranes.
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MEDLINE
Idioma:
En
Ano de publicação:
2018
Tipo de documento:
Article