Efficient Asymmetric Synthesis of Chiral Hydroxy-γ-butyrolactones

Iwan R Davies, M Cheeseman, R Green, Mary F Mahon, A Merritt, Steven D Bull

Research output: Contribution to journalArticle

15 Citations (Scopus)

Abstract

Treatment of β-vinyl-β-hydroxy-N-acyloxazolidin-2-ones with VO(acac)2 and tert-butyl hydroperoxide results in formation of unstable epoxides that are ring-opened by intramolecular nucleophilic attack of their exocyclic carbonyl fragments to afford highly functionalized trisubstituted hydroxy-γ-butyrolactones in >95% de, with a polymer-supported oxazolidin-2-one having been used to transfer this methodology to the solid phase.
Original languageEnglish
Pages (from-to)2896-2899
Number of pages4
JournalOrganic Letters
Volume11
Issue number13
DOIs
Publication statusPublished - 2009

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