An asymmetric, SmI2-mediated approach to γ-butyrolactones using a new, fluorous-tagged auxiliary

Johannes C. Vogel, Rebecca Butler, David J. Procter

Research output: Contribution to journalArticlepeer-review

15 Citations (Scopus)

Abstract

A new, fluorous-tagged chiral auxiliary has been developed for the asymmetric, SmI2-mediated coupling of aldehydes and α,β-unsaturated esters. γ-Butyrolactones are obtained in moderate to good isolated yield and in high enantiomeric excess. The fluorous tag allows the auxiliary to be conveniently recovered by fluorous solid-phase extraction (FSPE) and reused.

Original languageEnglish
Pages (from-to)11876-11883
Number of pages8
JournalTetrahedron
Volume64
Issue number52
DOIs
Publication statusPublished - 22 Dec 2008
Externally publishedYes

Keywords

  • Samarium
  • Radicals
  • Asymmetric
  • Fluorous
  • Lactones

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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