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

Byoungmoo Kim, Golo Storch, Gourab Banerjee, Brandon Q. Mercado, Janelle Castillo-Lora, Gary W. Brudvig, James M. Mayer, Scott J. Miller

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)15239-15244
Number of pages6
JournalJournal of the American Chemical Society
Volume139
Issue number42
DOIs
Publication statusPublished - Oct 25 2017

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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    Kim, B., Storch, G., Banerjee, G., Mercado, B. Q., Castillo-Lora, J., Brudvig, G. W., Mayer, J. M., & Miller, S. J. (2017). Stereodynamic Quinone-Hydroquinone Molecules That Enantiomerize at sp3-Carbon via Redox-Interconversion. Journal of the American Chemical Society, 139(42), 15239-15244. https://doi.org/10.1021/jacs.7b09176