Synthesis of a new iron Lewis acid catalyst possessing a chelating cyclopentadienyldiphenylphosphinite ligand, (η51-C5H4CH(Ph)OPPh2)

Michael F. Mayer, M. Mahmun Hossain

Research output: Contribution to journalArticlepeer-review

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Abstract

A new iron Lewis acid catalyst, [(η51-C5H4CH(Ph)OPPh2)Fe(CO)(THF)]+[BF4]- featuring a cyclopentadienyl ring that is tethered to a terminal diphenylphosphinite moiety was created. This is the first complex to contain a chelating η51- cyclopentadienyl-phosphinite ligand. This new racemic iron Lewis acid was tested and found to be an effective catalyst in an aziridine-forming reaction. An asymmetric alcohol that is a precursor of the chiral catalyst was synthesized with greater than 95% ee. Upon ligation of the diphenylphosphinite to the iron center, a 3:2 mixture of diastereomers was formed. The diastereomeric mixture of the asymmetric catalysts was utilized in the aziridine-forming reaction and produced the cis-aziridine with low enantiomeric excess.

Original languageEnglish
Pages (from-to)202-209
Number of pages8
JournalJournal of Organometallic Chemistry
Volume654
Issue number1-2
DOIs
StatePublished - Jul 15 2002

Keywords

  • Aziridines
  • Iron Lewis acid catalyst
  • η:η-cyclopentadienyl-phosphinite ligand

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