From pyrrolidin-2-ones to 3-aza-2-oxobicyclo[3.2.0]heptanes. Synthesis of both enantiomers of cis-2-aminomethylcyclobutane carboxylic acid, a conformationally restricted analogue of GABA

Roberta Galeazzi, Giovanna Mobbili, Mario Orena

Research output: Contribution to journalArticlepeer-review

Abstract

By changing the cyclisation conditions (NaH in THF or NaOEt in EtOH), an enantiopure malonamide containing an enoate acceptor afforded either diastereomeric pyrrolidin-2-one 3 or 4 as the major product of the intramolecular conjugate addition. After separation, both diastereomers were converted through simple steps into the corresponding 3-aza-2- oxobicyclo[3.2.0] heptane which eventually led to each enantiomer of cis-2- aminomethylcyclobutanecarboxylic acid, 1, a conformationally restricted analogue of GABA, in both enantiomerically pure form.

Original languageEnglish
Pages (from-to)261-270
Number of pages10
JournalTetrahedron
Volume55
Issue number1
DOIs
Publication statusPublished - Jan 1 1999

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

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