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Keywords:

  • aldol reactions;
  • cascade reactions;
  • diastereoselectivity;
  • haloketones;
  • polyketides
Thumbnail image of graphical abstract

Double-action haloketones: A super silyl group enabled the first highly diastereoselective Mukaiyama aldol reactions of α-chloro- and α-fluoroketones with a wide range of aldehydes, providing anti-β-siloxy-α-haloketones. This process is compatible with one-pot double-aldol methodology and allows for rapid access to new halogen-modified polyketide fragments bearing up to four contiguous stereocenters (see scheme).