Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 57, Issue 46, Pages 15107-15111Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201808305
Keywords
chirality; enantiomerization; quinones; redox chemistry; stereodynamics
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Funding
- National Institutes of Health [NIH R01-GM096403]
- Deutsche Forschungsgemeinschaft (DFG) [STO 1175/1-1]
- NATIONAL INSTITUTE OF GENERAL MEDICAL SCIENCES [R01GM096403] Funding Source: NIH RePORTER
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Reversible redox processes involving hydroquinones and quinones are ubiquitous in biological reaction networks, materials science, and catalysis. While extensively studied in intermolecular settings, less is known about intramolecular scenarios. Herein, we report hydroquinone-quinone hybrid molecules that form two-stereocenter dihydrobenzofurans via intramolecular cyclization under thermodynamic control. A pi-methylhistidine peptide-catalyzed kinetic resolution allowed us to study the stereodynamic behavior of enantio- and diastereo-enriched dihydrofurans. In the course of this study, it was revealed that a reversible intramolecular redox-interconversion network connects all four possible stereoisomers via inversion of a quaternary carbon stereocenter without achiral intermediates. As a result, these findings on hydroquinone-quinone hybrid molecules provide insights into potential natural origin and synthetic access of the common dihydrobenzofuran motif.
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