Template-induced enantioselectivity in the reductive radical cyclization of 3-(3-iodopropoxy)propenoic acid derivatives depending on the binding motif

Peter Kapitán, Thorsten Bach

Research output: Contribution to journalArticlepeer-review

13 Scopus citations

Abstract

Different binding motifs HXC=O have been screened in the enantioselective radical cyclization of various linear derivatives of 3-(3-iodopropoxy)propenoic acid. The reactions were performed in the presence of an enantiomerically pure, chiral 1,5,7-trimethyl-3-azabicyclo[3.3.1]nonan-2-one derivative, which acts as a hydrogen-binding template. The cyclized products were obtained in good to excellent yields (66-88%). Enantioselectivities up to 59% ee were achieved.

Original languageEnglish
Article numberZ04608SS
Pages (from-to)1559-1564
Number of pages6
JournalSynthesis
Issue number10
DOIs
StatePublished - 19 May 2008

Keywords

  • Cyclizations
  • Enantioselectivity
  • Lactams
  • Radical reactions
  • Supramolecular chemistry

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