Synthesis and reactivities of enantiomerically pure β hydroxyalkyl and β-aminoalkyl ferrocenyl sulfides

Luca Bernardi, Bianca F. Bonini, Mauro Comes-Franchini, Mariafrancesca Fochi, Germana Mazzanti, Alfredo Ricci, Greta Varchi

Research output: Contribution to journalArticlepeer-review

30 Scopus citations

Abstract

Enantiomerically pure β-hydroxyalkyl and β-aminoalkyl ferrocenyl sulfides have been synthesized in good yields from mercaptoferrocene and amino alcohol derivatives. Primary β-aminoalkyl sulfides allowed the synthesis of tetrahydro-1,4-thiazepines containing the ferrocene moiety with good diastereoselectivity and β-iminoalkyl sulfides. Some of these derivatives have successfully been employed as ligands for palladium-catalyzed allylic substitution, with asymmetric induction of up to 99% ee. (

Original languageEnglish (US)
Pages (from-to)2776-2784
Number of pages9
JournalEuropean Journal of Organic Chemistry
Issue number16
DOIs
StatePublished - Aug 2002

Keywords

  • Allylic substitution
  • Catalysis
  • Ferrocene
  • Palladium
  • Sandwich complexes
  • Sulfur

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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