Racemization and Deracemization through Intermolecular Redox Behaviour

Anthonius H.J. Engwerda, Hugo Meekes, F. Matthias Bickelhaupt, Floris P.J.T. Rutjes*, Elias Vlieg

*Corresponding author for this work

Research output: Contribution to JournalArticleAcademicpeer-review

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 languageEnglish
Pages (from-to)9639-9642
Number of pages4
JournalChemistry - A European Journal
Volume25
Issue number41
Early online date7 Jun 2019
DOIs
Publication statusPublished - 22 Jul 2019

Keywords

  • chiral resolution
  • deracemization
  • quinone
  • racemization
  • redox

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