Synthesis of chiral 1′-substituted oxazolinylferrocenes as chiral ligands for Pd-catalyzed allylic substitution reactions

Jaiwook Park, Zhenyu Quan, Sunwoo Lee, Kyo Han Ahn, Chang Woo Cho

Research output: Contribution to journalArticlepeer-review

49 Scopus citations

Abstract

Chiral 1-oxazolinyl-1′-(diphenylphosphino)ferrocenes 4 and 1-oxazolinyl-1′-(phenylthio)ferrocenes 5 were prepared from 1,1′-dibromoferrocene through 1-oxazolinyl-1′-bromoferrocenes 3. The compounds 4 and 5 were employed as chiral ligands in Pd-catalyzed asymmetric allylic substitution reactions. High enantioselectivities (82-99% ee) and high yields (96-99%) were observed in the substitution reactions of 1,3-diphenylprop-2-enyl acetate and dimethyl malonate with the catalysts generated from [(π-allyl)PdCl]2 and 4, while the use of 5 led to inferior results (20-75% ee and 25-28% yields). 1H-, 13C-, and 31P-NMR data are analyzed for the complexes obtained from the reactions of [(η3-allyl)PdCl]2 and [η3-1,3-diphenylallyl)PdCl]2 with 4a and 4b.

Original languageEnglish
Pages (from-to)140-146
Number of pages7
JournalJournal of Organometallic Chemistry
Volume584
Issue number1
DOIs
StatePublished - 10 Jul 1999

Keywords

  • 1′-Substituted oxazolinylferrocenes
  • Allylic substitution
  • N,P′-chelate
  • Pd-catalysts

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