Enantiopure isoindolinones through Viedma ripening

René R. E. Steendam, Maxime C. T. Brouwer, Evelien M. E. Huijs, Michaël W. Kulka, Hugo Meekes, Willem J. P. van Enckevort, Jan Raap, Floris P. J. T. Rutjes, Elias Vlieg

Research output: Contribution to journalArticle

15 Citations (Scopus)

Abstract

Here we demonstrate that deracemization of isoindolinones using Viedma ripening is possible starting from a racemic mixture of conglomerate crystals. Crystals of the enantiopure isoindolinones lose their chiral identity upon dissolution even without the need for a catalyst. This enabled complete deracemization of the reported isoindolinones without a catalyst.

LanguageEnglish
Pages13527-13530
Number of pages4
JournalChemistry - A European Journal
Volume20
Issue number42
DOIs
Publication statusPublished - 13 Oct 2014

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Crystals
Catalysts
Dissolution

Keywords

  • crystallization
  • isoindoles
  • solubility
  • stereoisomerism
  • asymmetric amplification
  • chiral resolution
  • chirality
  • grinding
  • heterocycles

Cite this

Steendam, R. R. E., Brouwer, M. C. T., Huijs, E. M. E., Kulka, M. W., Meekes, H., van Enckevort, W. J. P., ... Vlieg, E. (2014). Enantiopure isoindolinones through Viedma ripening. Chemistry - A European Journal, 20(42), 13527-13530. https://doi.org/10.1002/chem.201404320
Steendam, René R. E. ; Brouwer, Maxime C. T. ; Huijs, Evelien M. E. ; Kulka, Michaël W. ; Meekes, Hugo ; van Enckevort, Willem J. P. ; Raap, Jan ; Rutjes, Floris P. J. T. ; Vlieg, Elias. / Enantiopure isoindolinones through Viedma ripening. In: Chemistry - A European Journal. 2014 ; Vol. 20, No. 42. pp. 13527-13530.
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Steendam, RRE, Brouwer, MCT, Huijs, EME, Kulka, MW, Meekes, H, van Enckevort, WJP, Raap, J, Rutjes, FPJT & Vlieg, E 2014, 'Enantiopure isoindolinones through Viedma ripening' Chemistry - A European Journal, vol. 20, no. 42, pp. 13527-13530. https://doi.org/10.1002/chem.201404320

Enantiopure isoindolinones through Viedma ripening. / Steendam, René R. E.; Brouwer, Maxime C. T.; Huijs, Evelien M. E.; Kulka, Michaël W.; Meekes, Hugo; van Enckevort, Willem J. P.; Raap, Jan; Rutjes, Floris P. J. T.; Vlieg, Elias.

In: Chemistry - A European Journal, Vol. 20, No. 42, 13.10.2014, p. 13527-13530.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Enantiopure isoindolinones through Viedma ripening

AU - Steendam, René R. E.

AU - Brouwer, Maxime C. T.

AU - Huijs, Evelien M. E.

AU - Kulka, Michaël W.

AU - Meekes, Hugo

AU - van Enckevort, Willem J. P.

AU - Raap, Jan

AU - Rutjes, Floris P. J. T.

AU - Vlieg, Elias

N1 - © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

PY - 2014/10/13

Y1 - 2014/10/13

N2 - Here we demonstrate that deracemization of isoindolinones using Viedma ripening is possible starting from a racemic mixture of conglomerate crystals. Crystals of the enantiopure isoindolinones lose their chiral identity upon dissolution even without the need for a catalyst. This enabled complete deracemization of the reported isoindolinones without a catalyst.

AB - Here we demonstrate that deracemization of isoindolinones using Viedma ripening is possible starting from a racemic mixture of conglomerate crystals. Crystals of the enantiopure isoindolinones lose their chiral identity upon dissolution even without the need for a catalyst. This enabled complete deracemization of the reported isoindolinones without a catalyst.

KW - crystallization

KW - isoindoles

KW - solubility

KW - stereoisomerism

KW - asymmetric amplification

KW - chiral resolution

KW - chirality

KW - grinding

KW - heterocycles

U2 - 10.1002/chem.201404320

DO - 10.1002/chem.201404320

M3 - Article

VL - 20

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JO - Chemistry - A European Journal

T2 - Chemistry - A European Journal

JF - Chemistry - A European Journal

SN - 0947-6539

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ER -

Steendam RRE, Brouwer MCT, Huijs EME, Kulka MW, Meekes H, van Enckevort WJP et al. Enantiopure isoindolinones through Viedma ripening. Chemistry - A European Journal. 2014 Oct 13;20(42):13527-13530. https://doi.org/10.1002/chem.201404320