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

Roberta Galeazzi, Silvano Geremia, Giovanna Mobbili, Mario Orena

Research output: Contribution to journalArticle

20 Citations (Scopus)

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 languageEnglish
Pages (from-to)587-605
Number of pages19
JournalTetrahedron: Asymmetry
Volume10
Issue number3
DOIs
Publication statusPublished - Feb 16 1999

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Iodobenzoates
Molecular mechanics
X-Ray Diffraction
X ray diffraction analysis
Nuclear magnetic resonance
Derivatives
nuclear magnetic resonance
configurations
diffraction
x rays
potassium borohydride
Proton Magnetic Resonance Spectroscopy

ASJC Scopus subject areas

  • Inorganic Chemistry
  • Organic Chemistry
  • Materials Chemistry
  • Drug Discovery

Cite this

Stereoselective reduction of chiral trans-3-acetyl 4-alkylpyrrolidin-2- ones. / Galeazzi, Roberta; Geremia, Silvano; Mobbili, Giovanna; Orena, Mario.

In: Tetrahedron: Asymmetry, Vol. 10, No. 3, 16.02.1999, p. 587-605.

Research output: Contribution to journalArticle

Galeazzi, Roberta ; Geremia, Silvano ; Mobbili, Giovanna ; Orena, Mario. / Stereoselective reduction of chiral trans-3-acetyl 4-alkylpyrrolidin-2- ones. In: Tetrahedron: Asymmetry. 1999 ; Vol. 10, No. 3. pp. 587-605.
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