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Unnatural α-amino Ethyl Esters From Diethyl Malonate or Ethyl β-bromo-α-hydroxyiminocarboxylate

Unnatural α-amino Ethyl Esters From Diethyl Malonate or Ethyl β-bromo-α-hydroxyiminocarboxylate

Eloi P Coutant, Vincent Hervin, Glwadys Gagnot, Candice Ford, Racha Baatallah, Yves L Janin

Beilstein J Org Chem. 2018 Nov 16;14:2853-2860.

PMID: 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 β-bromo-α-hydroxyiminocarboxylate and various alkylfuranes.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP105533	Diethyl malonate		105-53-3	Price

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