224645-99-2Relevant academic research and scientific papers
Stereoselective reduction of chiral trans-3-acetyl 4-alkylpyrrolidin-2- ones
Galeazzi, Roberta,Geremia, Silvano,Mobbili, Giovanna,Orena, Mario
, p. 587 - 605 (2007/10/03)
A number of trans-3-acetyl-4-alkylpyrrolidin-2-ones 8a-d and 11a,b were prepared and reduction of the keto group, carried out with KBH4 in CH3OH, led mainly to 3-hydroxyethylpyrrolidin-2-ones 13a-d and 19a,b with high stereoselection. Configuration of the newly formed stereogenic centre on the hydroxyethyl chain was assigned by 1H NMR data supported by molecular mechanic calculations and eventually confirmed by X-ray diffraction analysis of p-iodobenzoate derivative 15.
Thermodynamic vs. kinetic control in the stereoselective intramolecular conjugate addition of amide enolates leading to chiral trans-3,4- disubstituted pyrrolidin-2-ones
Galeazzi, Roberta,Mobbili, Giovanna,Orena, Mario
, p. 4029 - 4042 (2007/10/03)
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.
