Abstract
Chiral molecules exhibiting a quinone and/or hydroquinone moiety are ubiquitous in natural products and small molecule drugs. Herein, we describe a chiral quinone-hydroquinone molecule that racemizes through a reversible redox reaction. Using a combined computational and experimental approach, we show that this racemization proceeds via an intermolecular reaction mechanism. Starting from two achiral reactants, this molecule could be obtained in enantiopure form using Viedma ripening.
| Original language | English |
|---|---|
| Pages (from-to) | 9639-9642 |
| Number of pages | 4 |
| Journal | Chemistry - A European Journal |
| Volume | 25 |
| Issue number | 41 |
| DOIs | |
| Publication status | Published - 22 Jul 2019 |
| Externally published | Yes |
Keywords
- chiral resolution
- deracemization
- quinone
- racemization
- redox
ASJC Scopus subject areas
- Catalysis
- Organic Chemistry
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