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

Chemistry. 2014 Oct 13;20(42):13527-30. doi: 10.1002/chem.201404320. Epub 2014 Aug 28.

Authors

René R E Steendam¹, 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

Affiliation

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

PMID: 25168197
DOI: 10.1002/chem.201404320

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: asymmetric amplification; chiral resolution; chirality; grinding; heterocycles.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Crystallization
Isoindoles / chemistry*
Solubility
Stereoisomerism

Substances

Isoindoles