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Keywords:

  • alkylation;
  • atropisomers;
  • Michael addition;
  • nucleophilic substitution;
  • organocatalysis
Thumbnail image of graphical abstract

Executive decision: Depending on the catalyst (both N-triflylphosphoramides), the highly enantioselective Brønsted acid catalyzed addition of indoles to α,β-unsaturated carbonyl compounds provides either α-keto esters (up to 92 % ee, left side of the scheme), or a novel type of bisindole (right), which displays atropisomerism. The α-keto esters can also be converted into amino acids by a one-pot 1,4-addition-reductive amination reaction.