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.
https://hal-pasteur.archives-ouvertes.fr/pasteur-01972143 Contributor : Yves JaninConnect in order to contact the contributor Submitted on : Monday, January 7, 2019 - 3:19:09 PM Last modification on : Monday, June 27, 2022 - 1:20:41 PM Long-term archiving on: : Monday, April 8, 2019 - 4:47:52 PM