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Keywords:

  • aniline derivatives;
  • asymmetric synthesis;
  • domino reactions;
  • organocatalysis;
  • quadruple cascade

Abstract

An organocatalytic quadruple domino reaction initiated by a Friedel–Crafts-type reaction of electron-rich arenes is described. The procedure involving up to three different Michael acceptors afforded highly functionalized cyclohexenecarbaldehydes bearing an aniline moiety, which are of great pharmaceutical and agricultural interest. This diphenylprolinol trimethylsilyl ether-catalyzed reaction also generates up to 4 contiguous stereocenters. It could be shown that various functional groups are tolerated and all products were obtained with very good diastereo- and excellent enantioselectivity.