Highly enantioselective rhodium-catalyzed asymmetric 1,4-addition reactions of arylboronic acids to acyclic α,β-unsaturated compounds: The formal synthesis of (-)-indatraline

Wei Ting Wei, Jiann Yih Yeh, Ting Shen Kuo, Hsyueh Liang Wu

Research output: Contribution to journalArticle

42 Citations (Scopus)

Abstract

It's do or diene: Stable chiral bicyclo[2.2.1]diene ligands were synthesized from (-)-5-oxobornyl acetate and utilized in the asymmetric 1,4-addition reaction of arylboronic acids with acyclic α,β- unsaturated compounds. Low catalytic loading of the complex, generated in situ from 1 and [{RhCl(C2H4)2}2], provides adducts in good to excellent yields and excellent enantioselectivities. This method was used for the formal total synthesis of (-)-indatraline.

Original languageEnglish
Pages (from-to)11405-11409
Number of pages5
JournalChemistry - A European Journal
Volume17
Issue number41
DOIs
Publication statusPublished - 2011 Oct 4

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Keywords

  • addition reactions
  • arylboronic acids
  • asymmetric catalysis
  • diene ligands
  • enantioselectivity
  • indatraline
  • rhodium

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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