Deracemization controlled by reaction-induced nucleation: viedma ripening as a safety catch for total spontaneous resolution

René R. E. Steendam, Tim J. B. van Benthem, Evelien M. E. Huijs, Hugo Meekes, Willem J. P. van Enckevort, Jan Raap, Floris P. J. T. Rutjes, Elias Vlieg

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Abstract

Viedma ripening was recently applied to a reaction enabling the conversion of achiral reactants in solution into enantiopure product crystals. Here we show that the configuration of the final product and the rate of deracemization are highly dependent on the initial crystal nucleation process or, if applied, seed crystals. Depending on the nucleation process, the transformation proceeds through total spontaneous resolution or Viedma ripening. Swift solid state deracemization can also be achieved using heating-cooling cycles as an alternative to Viedma ripening, provided that crystal nucleation results in a sufficiently high initial enantiomeric excess to trigger the deracemization process. (Chemical Equation Presented).

Original languageEnglish
Pages (from-to)3917-3921
Number of pages5
JournalCrystal Growth and Design
Volume15
Issue number8
Early online date16 Jun 2015
DOIs
Publication statusPublished - 5 Aug 2015
Externally publishedYes

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Keywords

  • chiral molecules
  • crystals
  • viedma ripening
  • crystalization

Cite this

Steendam, R. R. E., van Benthem, T. J. B., Huijs, E. M. E., Meekes, H., van Enckevort, W. J. P., Raap, J., ... Vlieg, E. (2015). Deracemization controlled by reaction-induced nucleation: viedma ripening as a safety catch for total spontaneous resolution. Crystal Growth and Design , 15(8), 3917-3921. https://doi.org/10.1021/acs.cgd.5b00531