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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.
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Submitted on : Monday, January 7, 2019 - 3:19:09 PM
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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, Beilstein-Institut, 2018, 14, pp.2853-2860. ⟨10.3762/bjoc.14.264⟩. ⟨pasteur-01972143⟩

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