94271-53-1

Upstream product

• 685-87-0 Diethyl 2-bromomalonate 
• 2393-23-9 4-methoxy-benzylamine 

Downstream Products

• 94271-45-1 1-(4-Methoxy-benzyl)-4-oxo-azetidine-2,2-dicarboxylic acid diethyl ester 
• 94271-48-4 2-[(2-Chloro-acetyl)-(4-methoxy-benzyl)-amino]-malonic acid diethyl ester 

Relevant academic research and scientific papers

Base-promoted c→n acyl rearrangement: An unconventional approach to α-amino acid derivatives

We have discovered that N-alkyl aminomalonates undergo a fast and selective intramolecular C→N acyl rearrangement reaction in the presence of a strong base, leading to N-protected glycinates in excellent yield. Moreover, the fact that the reaction proceeds through a nucleophilic enolate intermediate has been used for implementing a tandem rearrangement/alkylation sequence that has been applied to the preparation of synthetically relevant nonproteinogenic tertiary and quaternary N-alkyl α-amino acids in a very simple and reliable way.