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Synfacts 2019; 15(03): 0293
DOI: 10.1055/s-0037-1611212
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart · New York

Catalytic Deracemization of Allenes

Contributor(s):
Benjamin List
,
Yihang Li
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
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Further Information

Publication History

Publication Date:
15 February 2019 (online)

 
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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.


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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.


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