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Keywords:

  • amino acids;
  • chiral amines;
  • Mannich bases;
  • organocatalysis;
  • quaternary stereocenters
Thumbnail image of graphical abstract

You're in control of which diastereomer of a quaternary α-amino acid derivative is formed in a direct organocatalytic diastereoselective and enantioselective Mannich reaction of ketimines with aldehydes (see scheme). The reactions are high yielding and can be controlled through the choice of the catalyst to give either diastereomer of the product with diastereomeric ratios as high as >20:1 and with 83–98 % ee. Pg=protecting group.