Stereoselective reduction of chiral trans-3-acetyl 4-alkylpyrrolidin-2- ones

Roberta Galeazzi; Silvano Geremia; Giovanna Mobbili; Mario Orena

doi:10.1016/S0957-4166(99)00031-2

Stereoselective reduction of chiral trans-3-acetyl 4-alkylpyrrolidin-2- ones

Roberta Galeazzi, Silvano Geremia, Giovanna Mobbili, Mario Orena

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

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

Abstract

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.

Original language	English
Pages (from-to)	587-605
Number of pages	19
Journal	Tetrahedron: Asymmetry
Volume	10
Issue number	3
DOIs	https://doi.org/10.1016/S0957-4166(99)00031-2
Publication status	Published - Feb 16 1999

ASJC Scopus subject areas

Inorganic Chemistry
Organic Chemistry
Materials Chemistry
Drug Discovery

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

abstract = "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.",

author = "Roberta Galeazzi and Silvano Geremia and Giovanna Mobbili and Mario Orena",

year = "1999",

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T1 - Stereoselective reduction of chiral trans-3-acetyl 4-alkylpyrrolidin-2- ones

AU - Galeazzi, Roberta

AU - Geremia, Silvano

AU - Mobbili, Giovanna

AU - Orena, Mario

PY - 1999/2/16

Y1 - 1999/2/16

N2 - 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.

AB - 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.

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M3 - Article

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JO - Tetrahedron Asymmetry

JF - Tetrahedron Asymmetry

SN - 0957-4166

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ER -

Stereoselective reduction of chiral trans-3-acetyl 4-alkylpyrrolidin-2- ones

Abstract

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