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Keywords:

  • asymmetric synthesis;
  • octahydroacridines;
  • one-pot reactions;
  • organocatalysis;
  • Povarov reaction
Thumbnail image of graphical abstract

An elegant sequence: An efficient method for the formation of octahydroacridines provides high yields and a high level of stereogenic control, and displays great tolerance towards different aldehydes, anilines, and nucleophiles (see scheme; TMS=trimethylsilyl; EWG=electron-withdrawing group). The use of different nucleophiles verifies an endo transition state in which π–π overlap of the aromatic rings plays an important role in the reactivity and selectivity.