Cu(I)-Catalyzed Asymmetric Multicomponent Cascade Inverse Electron-Demand Aza-Diels-Alder/Nucleophilic Addition/Ring-Opening Reaction Involving 2-Methoxyfurans as Efficient Dienophiles

J Am Chem Soc. 2016 Mar 30;138(12):3998-4001. doi: 10.1021/jacs.6b01008. Epub 2016 Mar 18.

Abstract

An unprecedented multicomponent cascade asymmetric inverse-electron-demand Diels-Alder/nucleophilic addition/ring-opening reaction involving 2-methoxyfurans as efficient dienophiles was successfully developed with Cu(I)/(t)Bu-Box complex as the catalyst. A diverse array of tetrahydropyridazines containing unexpectedly stable γ-hydroxyl ester moiety was obtained in generally good yield with exclusive regioselectivity and excellent stereoselectivity.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Aza Compounds / chemistry*
  • Catalysis
  • Copper / chemistry*
  • Electrons*
  • Furans / chemistry*
  • Hydrazones / chemistry
  • Molecular Structure

Substances

  • Aza Compounds
  • Furans
  • Hydrazones
  • 2-methoxyfuran
  • Copper