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

René R E Steendam, Michaël W. Kulka, Hugo Meekes, Willem J P Van Enckevort, Jan Raap, Elias Vlieg, Floris P J T Rutjes

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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.

Original languageEnglish
Pages (from-to)7249-7252
Number of pages4
JournalEuropean Journal of Organic Chemistry
Volume2015
Issue number33
Early online date22 Oct 2015
DOIs
Publication statusPublished - 1 Nov 2015

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Keywords

  • chiral resolution
  • chirality
  • heterocycles
  • multicomponent reactions
  • synthesis design

Cite this

Steendam, R. R. E., Kulka, M. W., Meekes, H., Van Enckevort, W. J. P., Raap, J., Vlieg, E., & Rutjes, F. P. J. T. (2015). One-pot synthesis, crystallization and deracemization of isoindolinones from achiral reactants. European Journal of Organic Chemistry, 2015(33), 7249-7252. https://doi.org/10.1002/ejoc.201501191