Regio- and Enantioselective Copper-Catalyzed Allylic Alkylation of Ortho-Substituted Cinnamyl Bromides with Grignard Reagents

Nathalie C. van der Molen, Theodora D. Tiemersma-Wegman, Martín Fañanás-Mastral, Ben L. Feringa

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Abstract

A highly efficient method for the copper-catalyzed asymmetric allylic alkylation of ortho-substituted cinnamyl bromides with Grignard reagents is reported. The use of a catalytic system comprising CuBr center dot SMe2 and TaniaPhos as chiral ligands gives rise to a range of branched products with excellent regio- and enantioselectivity.

Original languageEnglish
Pages (from-to)4981-4984
Number of pages4
JournalJournal of Organic Chemistry
Volume80
Issue number10
DOIs
Publication statusPublished - 15-May-2015

Keywords

  • CONJUGATE ADDITION
  • CARBENE COMPLEXES
  • ARYLATION
  • CHLORIDES
  • HETEROCYCLES
  • LIGANDS

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