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Keywords:

  • conjugate addition;
  • diastereoselectivity;
  • enamines;
  • enones;
  • imines
Thumbnail image of graphical abstract

A convergent strategy for the synthesis of tricyclic imino alcohols was partly inspired by a postulated biosynthesis of galbulimima alkaloids. In this sequential α,α′ alkylation of unsymmetrical ketoimines, at least three stereocenters are created with a high level of diastereoselectivity. Organocatalytic and asymmetric variants of this methodology complement an organocuprate-based approach (see scheme).