195829-01-7

Upstream product

• 195828-92-3 2-[(R)-2-((S)-5-tert-Butoxycarbonyl-3-methyl-2-oxo-imidazolidin-1-yl)-1-methyl-2-oxo-ethyl]-malonic acid 
• 170704-11-7 2-[(R)-2-((S)-5-tert-Butoxycarbonyl-3-methyl-2-oxo-imidazolidin-1-yl)-1-methyl-2-oxo-ethyl]-malonic acid dibenzyl ester 
• 195828-75-2 tert.-butyl (4S)-1-methyl-3-(2-bromopropionyl)-2-oxo-imidazolidine-4-carboxylate 
• 195828-95-6 (S)-3-((R)-3-Carboxy-2-methyl-propionyl)-1-methyl-2-oxo-imidazolidine-4-carboxylic acid tert-butyl ester 
• 100-51-6 benzyl alcohol 

Relevant academic research and scientific papers

Dynamic Kinetic Resolution Utilizing 2-Oxoimidazolidine-4-carboxylate as a Chiral Auxiliary: Stereoselective Alkylation of α-Bromo Amides with Malonic Ester Enolates

Stereoselective carbon-carbon bond formation by dynamic kinetic resolution using tert-butyl (4S)-1-methyl-2-oxoimidazolidine-4-carboxylate (1) as a chiral auxiliary was developed. Reaction of a diastereomeric mixture of tert-butyl (4S)-3-[(2RS)-2-bromoacyl]-1-methyl-2-oxoimidazolidine-4-carboxylates (2) with a malonic ester enolate in HMPA predominantly afforded tert-butyl (4S)-3-[(2R)-2-alkyl-3,3-bis(alkoxycarbonyl)propionyl]-1-methyl-2- oxoimidazolidine-4-carboxylate [(S,R)-8] in good yields. The stereoselectivity of this reaction was in accordance with our working hypothesis based on the conformational analysis of 2 and elucidated the unique characteristics of 1 as a novel chiral auxiliary for dynamic kinetic resolution. The alkylated products (S,R)-8e,j,k were easily converted to chiral α-alkyl succinic acid derivatives and chiral β-amino acid derivatives, both of which have been known as key building blocks for the syntheses of a variety of biologically active compounds.