TY - JOUR
T1 - Stereoselective reductive amination of chiral trans-3-acetyl-4- alkylpyrrolidin-2-ones
AU - Fava, Cristiana
AU - Galeazzi, Roberta
AU - Mobbili, Giovanna
AU - Orena, Mario
PY - 2003/11/28
Y1 - 2003/11/28
N2 - trans-3-Acetyl-4-alkyl pyrrolidin-2-ones 5a,b and 8a,b undergo reductive amination with NaBH3(CN) in CH3OH in the presence of CH3COONH4. By acylation of the reaction product the corresponding 3-acylaminoethylpyrrolidin-2-ones 9a-c and 10a,b were obtained with total stereoselection. The configuration of the newly formed stereogenic centre at C-1″ of the acylaminoethyl chain was assigned on the basis of 1H NMR data supported by both molecular mechanics and quantomechanical calculations.
AB - trans-3-Acetyl-4-alkyl pyrrolidin-2-ones 5a,b and 8a,b undergo reductive amination with NaBH3(CN) in CH3OH in the presence of CH3COONH4. By acylation of the reaction product the corresponding 3-acylaminoethylpyrrolidin-2-ones 9a-c and 10a,b were obtained with total stereoselection. The configuration of the newly formed stereogenic centre at C-1″ of the acylaminoethyl chain was assigned on the basis of 1H NMR data supported by both molecular mechanics and quantomechanical calculations.
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U2 - 10.1016/j.tetasy.2003.08.024
DO - 10.1016/j.tetasy.2003.08.024
M3 - Article
AN - SCOPUS:0344585381
VL - 14
SP - 3697
EP - 3703
JO - Tetrahedron Asymmetry
JF - Tetrahedron Asymmetry
SN - 0957-4166
IS - 23
ER -