Design and Synthesis of Novel Chiral Dirhodium(II) Carboxylate Complexes for Asymmetric Cyclopropanation Reactions

Frady G. Adly, Michael Gardiner, Ashraf Ghanem

    Research output: Contribution to journalArticle

    41 Citations (Scopus)

    Abstract

    A novel approach to the design of dirhodium(II) tetracarboxylates derived from (S)-amino acid ligands is reported. The approach is founded on tailoring the steric influences of the overall catalyst structure by reducing the local symmetry of the ligand's N-heterocyclic tether. The application of the new approach has led to the uncovering of [Rh2(S-tertPTTL)4] as a new member of the dirhodium(II) family with extraordinary selectivity in cyclopropanation reactions. The stereoselectivity of [Rh2(S-tertPTTL)4] was found to be comparable to that of [Rh2(S-PTAD)4] (up to >99 % ee), with the extra benefit of being more synthetically accessible. Correlations based on X-ray structures to justify the observed enantioinduction are also discussed.
    Original languageEnglish
    Pages (from-to)3447-3461
    Number of pages15
    JournalChemistry - A European Journal
    Volume22
    Issue number10
    DOIs
    Publication statusPublished - 2016

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