ChemInform Abstract: New Syntheses of α-Amino Acids Based on N-Acylimino Acetates.
Abstract
The reaction of N-acylaminobromoacetates such as (I) or (IV) (via N-acylamino acetate intermediates) with higher (or mixed) cuprates, e.g. (II), trimethylsilyl enol ethers, e.g. (V), or β-dicarbonyl compounds, e.g. (VII), leads to a variety of amino acid derivatives such as (III), (VI), (VIII).
ChemInform Abstract
The reaction of N-acylaminobromoacetates such as (I) or (IV) (via N-acylamino acetate intermediates) with higher (or mixed) cuprates, e.g. (II), trimethylsilyl enol ethers, e.g. (V), or β-dicarbonyl compounds, e.g. (VII), leads to a variety of amino acid derivatives such as (III), (VI), (VIII). Removal of the N-acyl and ester groups provides the corresponding amino acids. In the case of the similarly prepared N-acyl amino acid esters (IX), both protecting groups are removed easily in one step using TFA. In the case of N-acetyl esters such as (XI), cleavage of the protecting group, after hydrolysis (e.g. → (XII)), and optical resolution can be achieved in one step using hog renal acylase (e.g. → (XIII)).
