Rhodium/chiral diene-catalyzed asymmetric 1,4-addition of arylboronic acids to chromones: A highly enantioselective pathway for accessing chiral flavanones

Qijie He, Chau Ming So, Zhaoxiang BIAN, Tamio Hayashi, Jun WANG*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

24 Citations (Scopus)

Abstract

Chromone has been noted to be one of the most challenging substrates in the asymmetric 1,4-addi-tion of α,β-unsaturated carbonyl compounds. By employing the rhodium complex associated with a chiral diene ligand, (R,R)-Ph-bod∗, the 1,4-addition of a variety of aryl-boronic acids was realized to give high yields of the corresponding flavanones with excellent enantioselectivities (≥97% ee, 99% ee for most substrates). Ring-opening side products, which would lead to erosion of product enantioselectivity, were not observed under the stated reaction conditions.

Original languageEnglish
Pages (from-to)540-543
Number of pages4
JournalChemistry - An Asian Journal
Volume10
Issue number3
DOIs
Publication statusPublished - Mar 2015

Scopus Subject Areas

  • Biochemistry
  • Organic Chemistry

User-Defined Keywords

  • 4-addition
  • Asymmetric 1
  • Chiral dienes
  • Chiral flavanones
  • Chromones
  • Rhodium catalysis

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