One-pot synthesis, crystallization and deracemization of isoindolinones from achiral reactants

Steendam, René R E and Kulka, Michaël W. and Meekes, Hugo and Van Enckevort, Willem J P and Raap, Jan and Vlieg, Elias and Rutjes, Floris P J T (2015) One-pot synthesis, crystallization and deracemization of isoindolinones from achiral reactants. European Journal of Organic Chemistry, 2015 (33). pp. 7249-7252. ISSN 1434-193X

[img]
Preview
Text (Steendam-etal-EJOC-2015-One-pot-synthesis-crystalization-and-deracemization-of-isoindolinones)
Steendam_etal_EJOC_2015_One_pot_synthesis_crystalization_and_deracemization_of_isoindolinones.pdf
Accepted Author Manuscript

Download (380kB)| Preview

    Abstract

    The synthesis, crystallization, and complete solid-state deracemization of isoindolinones was realized in one pot simply by grinding achiral reaction components in a suitable solvent with an achiral catalyst. Previously, this concept was applied to a reversible reaction, but herein we showed that it could also be used in combination with reactions in which product formation is irreversible. A controlled final configuration of the product was obtained by using small amounts of chiral additives or seed crystals of the product.