An atom efficient synthesis of tamoxifen

Dorus Heijnen, Milan van Zuijlen, Filippo Tosi, Ben L. Feringa*

*Corresponding author for this work

Research output: Contribution to journalArticleAcademicpeer-review

5 Citations (Scopus)
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Abstract

The direct carbolithiation of diphenylacetylenes and their cross-coupling procedure taking advantage of the intermediate alkenyllithium reagents are presented. By employing our recently discovered highly active palladium nanoparticle based catalyst, we were able to couple an alkenyllithium reagent with a high (Z/E) selectivity (10 : 1) and good yield to give the breast cancer drug tamoxifen in just 2 steps from commercially available starting materials and with excellent atom economy and reaction mass efficiency.

Original languageEnglish
Pages (from-to)2315-2320
Number of pages6
JournalOrganic & Biomolecular Chemistry
Volume17
Issue number9
DOIs
Publication statusPublished - 7-Mar-2019

Keywords

  • 3-COMPONENT COUPLING REACTION
  • STEREOSELECTIVE-SYNTHESIS
  • GRIGNARD-REAGENTS
  • INTRAMOLECULAR CARBOLITHIATION
  • ORGANOLITHIUM COMPOUNDS
  • ARYL HALIDES
  • PALLADIUM
  • ALKYNES
  • (Z)-TAMOXIFEN
  • DERIVATIVES

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