175844-92-5

Upstream product

• 206358-45-4 (2'RS,4S,5R)-1-N-(2'bromopropanoyl)-3,4-dimethyl-5-phenylimidazolidin-2-one 
• 92841-65-1 (4R,5S)-1,5-dimethyl-4-phenylimidazolidin-2-one 
• 206358-46-5 (2'RS,4S,5R)-1-N-(2'-iodopropanoyl)-3,4-dimethyl-5-phenylimidazolidin-2-one 
• 100-46-9 benzylamine 
• 175844-90-3 (4R,5S,2'R)-3-(α-bromopropionyl)-1,5-dimethyl-4-phenylimidazolidin-2-one 

Downstream Products

• 31022-10-3 N-benzyl-L-alanine methyl ester 
• 92841-65-1 (4R,5S)-1,5-dimethyl-4-phenylimidazolidin-2-one 
• 120571-58-6 N-benzyl D-alanine methyl ester 
• 175844-90-3 (4R,5S,2'R)-3-(α-bromopropionyl)-1,5-dimethyl-4-phenylimidazolidin-2-one 
• 176018-05-6 (4R,5S,2'S)-3-(α-bromopropionyl)-1,5-dimethyl-4-phenylimidazolidin-2-one 
• 169219-76-5 (4S,5R)-1-N-(phenylacetyl)-3,4-dimethyl-5-phenyl-imidazolidin-2-one 

Relevant academic research and scientific papers

Rationalising diastereoselection in the dynamic kinetic resolution of α-haloacyl imidazolidinones

A crossover from S(N)2 to general base catalysed nucleophilic substitution can account for the dichotomous diastereoselectivity observed in DKR reactions of α-haloacyl imidazolidinones. Aprotic nucleophiles (Nu-) react preferentially with the 5S,2'R diastereomer via an S(N)2 mechanism. Conversely, amines (R2NH) generally react preferentially with the 5S,2'S diastereomer. General base catalysis via a bifurcated hydrogen bonded assembly accounts for this anomalous stereoselectivity.

A new dynamic resolution strategy for asymmetric synthesis

Two different and complementary auxiliary based dynamic resolution processes have been developed; the use of crystallisation induced dynamic resolution and/or dynamic kinetic resolution enables the preparation of either enantiomeric product using a single chiral auxiliary as illustrated in the preparation of D or L-alinine derivatives.