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Unnatural ?-amino ethyl esters from diethyl malonate or ethyl ?-bromo-?-hydroxyiminocarboxylate.

ABSTRACT: We have explored here the scope of the age-old diethyl malonate-based accesses to ?-amino esters involving Knoevenagel condensations of diethyl malonate on aldehydes, reductions of the resulting alkylidenemalonates, the preparation of the corresponding ?-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 ?-amino esters. Moreover, other pathways to ?-hydroxyimino esters were explored including an attempt to improve the cycloadditions between ethyl ?-bromo-?-hydroxyiminocarboxylate and various alkylfuranes.

SUBMITTER: Coutant EP 

PROVIDER: S-EPMC6244313 | biostudies-literature | 2018

REPOSITORIES: biostudies-literature

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

Coutant Eloi P EP   Hervin Vincent V   Gagnot Glwadys G   Ford Candice C   Baatallah Racha R   Janin Yves L YL  

Beilstein journal of organic chemistry 20181116

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 cyc  ...[more]

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