Chiral 3-hydroxypyrrolidin-2-ones from a Baylis-Hillman adduct: Convergent, stereoselective synthesis of a glycosidase inhibitor

Roberta Galeazzi, Gianluca Martelli, Giovanna Mobbili, Mario Orena, Samuele Rinaldi

Research output: Contribution to journalArticle

Abstract

The O-silyl derivative 4b, prepared starting from the Baylis-Hillman adduct 4a, underwent cyclization on treatment with (S)-phenylethylamine, to give to an equimolar mixture of the 4,5-cis-disubstituted pyrrolidin-2-ones 9 and 10, exclusively, which after separation by silica gel chromatography were both converted into the 3-hydroxy-4-hydroxymethylpyrrolidine 1 a glycosidase inhibitor.

Original languageEnglish
Pages (from-to)3249-3256
Number of pages8
JournalTetrahedron: Asymmetry
Volume15
Issue number20
DOIs
Publication statusPublished - Oct 18 2004

ASJC Scopus subject areas

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

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