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Keywords:

  • chirality;
  • density functional calculations;
  • small ring systems;
  • stereomutation;
  • transition states
Thumbnail image of graphical abstract

Synthetic chemists are challenged to find a five-atom molecule that, like cyclo-SeSSOS, can enantiomerize in a single step without passing through any achiral conformation. The barrier for the pseudorotation of cyclo-SeSSOS shown below is computed to be quite low: 6.2 kcal mol−1.