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Keywords:

  • asymmetric catalysis;
  • Michael addition;
  • nitroolefins;
  • organocatalysis;
  • synthetic methods
Thumbnail image of graphical abstract

Acetaldehyde, now a big contender: A silyl prolinol derivative was found to catalyze the first Michael addition of acetaldehyde with both aromatic and aliphatic nitroolefins in excellent enantioselectivities (see scheme, TMS=trimethylsilyl). The utility of the reaction is illustrated in the synthesis of three current pharmaceuticals and in the synthesis of an enantiopure 3-monosubstituted pyrrolidine.