Stereoselective reductive amination of chiral trans-3-acetyl-4- alkylpyrrolidin-2-ones

Cristiana Fava; Roberta Galeazzi; Giovanna Mobbili; Mario Orena

doi:10.1016/j.tetasy.2003.08.024

Stereoselective reductive amination of chiral trans-3-acetyl-4- alkylpyrrolidin-2-ones

Cristiana Fava, Roberta Galeazzi, Giovanna Mobbili, Mario Orena

Istituto Nazionale di Riposo e Cura per Anziani V.E. II

Research output: Contribution to journal › Article › peer-review

Abstract

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.

Original language	English
Pages (from-to)	3697-3703
Number of pages	7
Journal	Tetrahedron: Asymmetry
Volume	14
Issue number	23
DOIs	https://doi.org/10.1016/j.tetasy.2003.08.024
Publication status	Published - Nov 28 2003

ASJC Scopus subject areas

Inorganic Chemistry
Organic Chemistry
Materials Chemistry
Drug Discovery

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title = "Stereoselective reductive amination of chiral trans-3-acetyl-4- alkylpyrrolidin-2-ones",

abstract = "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.",

author = "Cristiana Fava and Roberta Galeazzi and Giovanna Mobbili and Mario Orena",

year = "2003",

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doi = "10.1016/j.tetasy.2003.08.024",

language = "English",

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journal = "Tetrahedron Asymmetry",

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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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DO - 10.1016/j.tetasy.2003.08.024

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JO - Tetrahedron Asymmetry

JF - Tetrahedron Asymmetry

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