Asymmetric allylation of unsymmetrical 1,3-diketones using a BINAP-palladium catalyst

Ryoichi Kuwano, Kei Ichi Uchida, Yoshihiko Ito

Research output: Contribution to journalArticle

62 Citations (Scopus)

Abstract

(Matrix presented) The chiral palladium complex generated in situ from [Pd(η3-allyl)Cl]2 and (R)-BINAP is a good catalyst for the catalytic asymmetric allylation of 1,3-diketones. The reaction provided chiral 2,2-dialkyl-1,3-diketones with 64-89% ee in high yields (13 examples). Enantiomeric excesses are strongly affected by the γ-substituent of the allylic substrates. A variety of unsymmetrical 1,3-diketones were alkylated with cinnamyl acetate in good enantioselectivities via use of the BINAP-palladium catalyst (77-89% ee).

Original languageEnglish
Pages (from-to)2177-2179
Number of pages3
JournalOrganic Letters
Volume5
Issue number12
DOIs
Publication statusPublished - Jun 12 2003

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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