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Racemization and Deracemization through Intermolecular Redox Behaviour.

Anthonius H J Engwerda1, Hugo Meekes1, F Matthias Bickelhaupt1,2

  • 1Institute for Molecules and Materials, Radboud University, Heyendaalseweg 135, 6525 AJ, Nijmegen, The Netherlands.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|June 8, 2019
PubMed
Summary
This summary is machine-generated.

A novel chiral quinone-hydroquinone molecule racemizes via a reversible redox reaction. This process was shown to be intermolecular, and enantiopure forms were achieved using Viedma ripening.

Keywords:
chiral resolutionderacemizationquinoneracemizationredox

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Area of Science:

  • Organic Chemistry
  • Supramolecular Chemistry
  • Chemical Crystallography

Background:

  • Chiral quinone and hydroquinone moieties are prevalent in natural products and pharmaceuticals.
  • Understanding racemization mechanisms is crucial for drug development and synthesis.

Purpose of the Study:

  • To describe a novel chiral quinone-hydroquinone molecule.
  • To elucidate the mechanism of its racemization.
  • To demonstrate a method for obtaining the molecule in enantiopure form.

Main Methods:

  • Combined computational and experimental approaches were utilized.
  • The racemization mechanism was investigated.
  • Viedma ripening was employed for enantiopure synthesis.

Main Results:

  • A chiral quinone-hydroquinone molecule capable of racemization via a reversible redox reaction was identified.
  • The racemization was confirmed to proceed through an intermolecular reaction mechanism.
  • Enantiopure forms of the molecule were successfully obtained from achiral precursors using Viedma ripening.

Conclusions:

  • The study presents a unique chiral molecule with a redox-driven racemization pathway.
  • The findings offer insights into the intermolecular mechanisms governing racemization in chiral quinones.
  • Viedma ripening provides an effective strategy for the enantioselective synthesis of such molecules.