166903-69-1

Upstream product

• 195828-76-3 tert.-butyl (4S)-1-methyl-3-(2-bromo-n-butyryl)-2-oxo-imidazolidine-4-carboxylate 
• 100-46-9 benzylamine 

Downstream Products

• 205748-36-3 methyl (R)-2-(N,N-dibenzylamino)butanoate 
• 205748-35-2 (S)-3-((R)-2-Dibenzylamino-butyryl)-1-methyl-2-oxo-imidazolidine-4-carboxylic acid tert-butyl ester 

Relevant academic research and scientific papers

Stereospecific Amination by Dynamic Kinetic Resolution Utilizing 2-Oxoimidazolidine-4-carboxylate as a Novel Chiral Auxiliary

A novel type of stereospecific amination by dynamic kinetic resolution using (4S)-2-oxoimidazolidine-4-carboxylate (1) as a chiral auxiliary was developed. A reaction of a diastereomeric mixture of (4S)-3--2-oxoimidazolidine-4-carboxylates 4 with an amine in the presence of a base in HMPA predominantly afforded (4S)-3--2-oxoimidazolidine-4-carboxylates (S,R)-7 in good yields.The reaction proceeded by stereospecific SN2 type amination incorporated with rapid interconversion between the substrates (S,S)-4 and (S,R)-4.Mechanistic study suggested that the unique stereoselectivity was induced through the interaction between an amine and the ester group of (S,S)-4 in the transition state.The chiral auxiliary was easily removed with alkoxide anion to afford the α-amino acid synthon in good yields.