175287-49-7

Upstream product

• 37517-81-0 3-chloro-3-oxopropanoic acid methyl ester 
• 171196-82-0 (S)-N-<3-ethoxycarbonyl-2(E)-propen-1-yl>-N-(1-phenyleth-1-yl)amine 
• 38330-80-2 monomethyl monopotassium malonate 

Downstream Products

• 175418-41-4 methyl (3S,4S,1'S)-[3-methoxycarbonyl-2-oxo-1-(1'-phenyleth-1'-yl)pyrrolidin-4-yl]acetate 
• 175287-53-3 methyl (3R,4R,1'S)-[3-methoxycarbonyl-2-oxo-1-(1'-phenyleth-1'-yl)pyrrolidin-4-yl]acetate 
• 174676-79-0 methyl (3R,1'S)-<1-(1'-phenyleth-1'-yl)-pyrrolidin-3-yl> acetate 
• 174676-82-5 methyl (3S,1'S)-<1-(1'-phenyleth-1'-yl)-pyrrolidin-3-yl> acetate 
• 174676-78-9 methyl (4R,1'S)-<2-oxo-1-(1'-phenyleth-1'-yl)pyrrolidin-4-yl>acetate 
• 174676-81-4 methyl (4S,1'S)-<2-oxo-1-(1'-phenyleth-1'-yl)pyrrolidin-4-yl>acetate 
• 122442-01-7 (R)-(-)-3-pyrrolidineacetic acid 
• 122442-02-8 (S)-(+)-homo-β-proline 

Relevant academic research and scientific papers

Thermodynamic vs. kinetic control in the stereoselective intramolecular conjugate addition of amide enolates leading to chiral trans-3,4- disubstituted pyrrolidin-2-ones

Intramolecular conjugate addition of amide enolates to α,β- unsaturated esters was found to give either of the diastereomeric trans-3,4- disubstituted pyrrolidin-2-ones 6, 10 or 7, 11 as the major products, by choosing the appropriate reaction conditions. The cyclisation performed with NaH in THF afforded mainly 6 and 10, whereas by using sodium ethoxide in ethanol the major products of the cyclisation were isomers 7 and 11, with the opposite configuration at both C-3 and C-4. This behaviour was explained by thermodynamic vs. kinetic control and supported by molecular mechanics and quantomechanical calculations.

Diastereomerically pure pyrrolidin-2-ones by intramolecular Michael reaction. Synthesis of both (S)- and (R)-3-pyrrolidineacetic acid

By intramolecular conjugate addition of their derived enolates, the amides 5 and 6 gave diastereomeric mixtures of pyrrolidin-2-ones 10,11 and 12,13, in good yield and 80:20 d.r. After chromatographic separation, the configuration of pure diastereomers wa