56598-99-3

Upstream product

• 685-87-0 Diethyl 2-bromomalonate 
• 100-46-9 benzylamine 
• 56599-00-9 diethyl N-benzyl-2-aminomalonate 

Downstream Products

• 6436-90-4 ethyl 2-(benzylamino)acetate 
• 64892-53-1 N-benzylalanine ethyl ester 
• 156865-68-8 ethyl 2-(benzylamino)butanoate 
• 99948-39-7 ethyl 2-(benzylamino)pent-4-enoate 
• 746551-67-7 diethyl 2-(benzylamino)succinate 
• 86694-79-3 diethyl 1-benzyl-4-oxoazetidine-2,2-dicarboxylate 
• 86694-81-7 1-benzyl-4-(mesyloxymethyl)-2-azetidinone 
• 86694-80-6 ethyl 4-oxo-1-(phenylmethyl)-2-azetidinecarboxylate 
• 85390-46-1 1-Benzyl-4-(hydroxymethyl)azetidin-2-one 
• 86694-78-2 diethyl N-benzyl-N-(chloroacetyl)aminomalonate 

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.