Enantioselective friedel-crafts alkylations catalyzed by bis(oxazolinyl)pyridine-scandium(III) triflate complexes

David A. Evans*, Keith R. Fandrick, Hyun Ji Song, Karl A. Scheidt, Risheng Xu

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

224 Scopus citations

Abstract

The enantioselective Friedel-Crafts addition of a variety of indoles catalyzed by bis(oxazolinyl)pyridine-scandium(III) triflate complexes (Sc(III)-pybox) was accomplished utilizing a series of β-substituted α,β-unsaturated phosphonates and α,β-unsaturated 2-acyl imidazoles. The acyl phosphonate products were efficiently transformed into esters and amides, whereas the acyl imidazole adducts were converted to a broader spectrum of functionalities such as esters, amides, carboxylic acids, ketones, and aldehydes. The sense of stereoinduction and level of enantioselectivity were found to be functions of the size of the substrate employed, the substitution on the ligand, and the catalyst loading. Molecular modeling of the catalyst with the bound substrates was performed based on the crystal structures of the catalyst complexes and the sense of stereoinduction observed in the addition reaction. Nonlinear effects over a range of catalyst concentrations implicate a mononuclear complex as the active catalyst.

Original languageEnglish (US)
Pages (from-to)10029-10041
Number of pages13
JournalJournal of the American Chemical Society
Volume129
Issue number32
DOIs
StatePublished - Aug 15 2007

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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