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

Research output: Journal article publicationJournal articleAcademic researchpeer-review

25 Citations (Scopus)

Abstract

kgaa, Weinheim. 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 - 1 Jan 2015
Externally publishedYes

Keywords

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

ASJC Scopus subject areas

  • Chemistry(all)

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