Enantioselective construction of 2,3-dihydrofuro[2,3-b]quinolines through supramolecular hydrogen bonding interactions

Fangrui Zhong, Thorsten Bach

Research output: Contribution to journalArticlepeer-review

24 Scopus citations

Abstract

The first asymmetric synthesis of 2,3-dihydrofuro[2,3-b]quinolines has been achieved by a cascade asymmetric aziridination/intramolecular ring-opening process of differently substituted 3-alkenylquinolones. Good yields and high enantioselectivities (up to 78% yield and 95% ee) were recorded when employing 2,2,2-trichloroethoxysulfonamide as the nitrene source, PhI(OCOtBu)2 as the oxidant, and a chiral C2 -symmetric Rh(II) complex as the catalyst (1 mol%). The catalyst bears two lactam motifs, which serve as binding sites for substrate coordination through supramolecular hydrogen-bonding interactions.

Original languageEnglish
Pages (from-to)13522-13526
Number of pages5
JournalChemistry - A European Journal
Volume20
Issue number42
DOIs
StatePublished - 13 Oct 2014

Keywords

  • asymmetric catalysis
  • enantioselectivity
  • hydrogen bonding
  • nitrogen heterocycles
  • rhodium

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