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

Steendam, René R. E. and van Benthem, Tim J. B. and Huijs, Evelien M. E. and Meekes, Hugo and van Enckevort, Willem J. P. and Raap, Jan and Rutjes, Floris P. J. T. and Vlieg, Elias (2015) Deracemization controlled by reaction-induced nucleation : viedma ripening as a safety catch for total spontaneous resolution. Crystal Growth and Design, 15 (8). pp. 3917-3921. ISSN 1528-7483 (https://doi.org/10.1021/acs.cgd.5b00531)

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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).

ORCID iDs

Steendam, René R. E. ORCID logoORCID: https://orcid.org/0000-0002-3363-4160, van Benthem, Tim J. B., Huijs, Evelien M. E., Meekes, Hugo, van Enckevort, Willem J. P., Raap, Jan, Rutjes, Floris P. J. T. and Vlieg, Elias;
  • Item type:Article
    ID code:58437
    Dates:
    Date
    Event
    5 August 2015
    Published
    16 June 2015
    Published Online
    16 June 2015
    Accepted
    Subjects:Science > Chemistry
    Medicine > Pharmacy and materia medica
    Department:UNSPECIFIED
    Depositing user: Pure Administrator
    Date deposited:02 Nov 2016 13:07
    Last modified:11 Nov 2024 11:20
    Related URLs:
    URI:https://strathprints.strath.ac.uk/id/eprint/58437
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