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Keywords:

  • aldehydes;
  • aldol reaction;
  • carbohydrates;
  • enantioselectivity;
  • homogeneous catalysis
Thumbnail image of graphical abstract

Two-faced: α-Oxyaldehydes can act as both an aldol donor and an aldol acceptor and can be coupled enantioselectively by using proline as the reaction catalyst. This new aldol reaction provides an operationally simple protocol for the stereocontrolled production of erythrose (see scheme) architecture and sets the stage for a two-step enantioselective synthesis of carbohydrates.