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

Roberta Galeazzi, Silvano Geremia, Giovanna Mobbili, Mario Orena

Research output: Contribution to journalArticle

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

ASJC Scopus subject areas

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

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