A Five-Atom Molecule which Enantiomerizes in a Single Step via Chiral Transition States


  • This work was supported the DFG, the VW foundation, and the Fonds der Chemischen Industrie. We thank Kurt Mislow (Princeton), Paul Mezey (Saskatoon), David Avnir (Jerusalem), and Martin Quack (Zürich) for helpful discussions and suggestions as well as for permission to cite unpublished results.


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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.