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

doi:10.1002/chem.201404320

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

Strathclyde Institute Of Pharmacy And Biomedical Sciences

Research output: Contribution to journal › Article

16 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.

Original language	English
Pages (from-to)	13527-13530
Number of pages	4
Journal	Chemistry - A European Journal
Volume	20
Issue number	42
DOIs	https://doi.org/10.1002/chem.201404320
Publication status	Published - 13 Oct 2014

Keywords

crystallization
isoindoles
solubility
stereoisomerism
asymmetric amplification
chiral resolution
chirality
grinding
heterocycles

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10.1002/chem.201404320

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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

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title = "Enantiopure isoindolinones through Viedma ripening",

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.",

keywords = "crystallization, isoindoles, solubility, stereoisomerism, asymmetric amplification, chiral resolution, chirality, grinding, heterocycles",

author = "Steendam, {Ren{\'e} R. E.} and Brouwer, {Maxime C. T.} and Huijs, {Evelien M. E.} and Kulka, {Micha{\"e}l W.} and Hugo Meekes and {van Enckevort}, {Willem J. P.} and Jan Raap and Rutjes, {Floris P. J. T.} and Elias Vlieg",

note = "{\circledC} 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.",

year = "2014",

month = "10",

day = "13",

doi = "10.1002/chem.201404320",

language = "English",

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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

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

C2 - 25168197

VL - 20

SP - 13527

EP - 13530

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

SN - 0947-6539

IS - 42

ER -