189098-09-7

Upstream product

• 100-52-7 benzaldehyde 
• 189098-08-6 (S)-ethyl 4,4-dimethyl-N-propionylpyroglutamate 
• 144978-35-8 (S)-ethyl N-tert-butoxycarbonylpyroglutamate 
• 158392-80-4 1-tert-butyl 2-ethyl (2S)4,4-dimethyl-5-oxopyrrolidine-1,2-dicarboxylate 
• 221637-35-0 (S)-ethyl 4,4-dimethyl-5-oxopyrrolidine-2-carboxylate 

Downstream Products

• 189098-10-0 ethyl (2R,3R)-3-phenyl-3-hydroxy-2-methylpropionate 
• 136312-66-8 (2R,3R)-3-hydroxy-2-methyl-3-phenylpropionic acid benzyl ester 
• 76549-04-7 (2R,3R)-(+)-3-hydroxy-2-methyl-3-phenylpropanoic acid 

Relevant academic research and scientific papers

(S)-Ethyl 4,4-dimethyl pyroglutamate as a new 'quat' chiral auxiliary in aldol condensations

Enolates I, derived from the N-propionyl derivative of the 'quat' chiral auxiliary (S)-ethyl 4,4-dimethyl pyroglutamate 4 undergo highly stereoselective aldol reactions, which upon hydrolysis and removal of the chiral auxiliary yields the (2R,3R)-3-hydrox

Chemoselective Nucleophilic Attack on N-Acyl Derivatives of (S)-Ethyl 4,4-Dimethyl Pyroglutamate (DMPG)

(Matrix presented) Heteronucleophiles and C-nucleophiles chemoselectively react with N-acyl (S)-ethyl 4,4-dimethyl pyroglutamate (DMPG) affording esters, amides, and ketones in high yield. The intramolecular process allows the stereoselective formation of β-hydroxy acids likely by formation and ring opening of the corresponding β-lactones.