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

Cristiana Fava, Roberta Galeazzi, Giovanna Mobbili, Mario Orena

Research output: Contribution to journalArticlepeer-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 languageEnglish
Pages (from-to)3697-3703
Number of pages7
JournalTetrahedron: Asymmetry
Volume14
Issue number23
DOIs
Publication statusPublished - Nov 28 2003

ASJC Scopus subject areas

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

Fingerprint Dive into the research topics of 'Stereoselective reductive amination of chiral trans-3-acetyl-4- alkylpyrrolidin-2-ones'. Together they form a unique fingerprint.

Cite this