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J Am Chem Soc. 2017 Oct 25;139(42):15239-15244. doi: 10.1021/jacs.7b09176. Epub 2017 Oct 11.

Stereodynamic Quinone-Hydroquinone Molecules That Enantiomerize at sp3-Carbon via Redox-Interconversion.

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Department of Chemistry, Yale University , New Haven, Connecticut 06520-8107, United States.


Since the discovery of molecular chirality, nonsuperimposable mirror-image organic molecules have been found to be essential across biological and chemical processes and increasingly in materials science. Generally, carbon centers containing four different substituents are configurationally stable, unless bonds to the stereogenic carbon atom are broken and re-formed. Herein, we describe sp3-stereogenic carbon-bearing molecules that dynamically isomerize, interconverting between enantiomers without cleavage of a constituent bond, nor through remote functional group migration. The stereodynamic molecules were designed to contain a pair of redox-active substituents, quinone and hydroquinone groups, which allow the enantiomerization to occur via redox-interconversion. In the presence of an enantiopure host, these molecules undergo a deracemization process that allows observation of enantiomerically enriched compounds. This work reveals a fundamentally distinct enantiomerization pathway available to chiral compounds, coupling redox-interconversion to chirality.

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