Hölzl-Hobmeier A,
Bauer A,
Silva AV,
Huber SM,
Bannwarth C,
Bach T.
* Technische Universität München, Ruhr-Universität Bochum and Universität Bonn, Germany
Catalytic Deracemization of Chiral Allenes by Sensitized Excitation with Visible Light.
Nature 2018;
564: 240-242
Key words
photocatalysis - deracemization - allenes - sensitized excitation
Significance
Bach and co-workers report an allene deracemization reaction catalyzed by an organic
chiral sensitizer under visible light. By using this method, several racemic allenes
were converted into enantiomers with yields of ≤100% and er values of ≤98.5:1.5. DFT
calculations are also provided to support the proposed mechanistic description.
Comment
Light-driven deracemization of chiral compounds might be implicated in the origin
of early-stage chirality. The present unprecedented discovery presents an example
to support this hypothesis. With different substrate classes, solutions to generate
chiral centers might be possible in cases where thermally controlled catalytic deracemizations
are entropically disfavored.
