Diastereomerically pure pyrrolidin-2-ones by intramolecular Michael reaction. Synthesis of both (S)- and (R)-3-pyrrolidineacetic acid

Roberta Galeazzi, Silvano Geremia, Giovanna Mobbili, Mario Orena

Research output: Contribution to journalArticlepeer-review

Abstract

By intramolecular conjugate addition of their derived enolates, the amides 5 and 6 gave diastereomeric mixtures of pyrrolidin-2-ones 10,11 and 12,13, in good yield and 80:20 d.r. After chromatographic separation, the configuration of pure diastereomers was assigned from 1H NMR data. The usefulness of this intramolecular cyclisation was proven by conversion of either 10 or 12 into pyrrolidin-2-one 14 which through simple steps gave (S)-3-pyrrolidineacetic acid, 2. Following the same synthetic scheme, but starting from either 11 or 13, (R)-3-pyrrolidineacetic acid 3 was obtained.

Original languageEnglish
Pages (from-to)79-88
Number of pages10
JournalTetrahedron: Asymmetry
Volume7
Issue number1
DOIs
Publication statusPublished - 1996

ASJC Scopus subject areas

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

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