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

doi:10.1002/ejoc.201501191

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

Strathclyde Institute Of Pharmacy And Biomedical Sciences

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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 language	English
Pages (from-to)	7249-7252
Number of pages	4
Journal	European Journal of Organic Chemistry
Volume	2015
Issue number	33
Early online date	22 Oct 2015
DOIs	https://doi.org/10.1002/ejoc.201501191
Publication status	Published - 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

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AU - Steendam, René R E

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AU - Van Enckevort, Willem J P

AU - Raap, Jan

AU - Vlieg, Elias

AU - Rutjes, Floris P J T

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N2 - 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.

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KW - multicomponent reactions

KW - synthesis design

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Access to Document

10.1002/ejoc.201501191

Steendam-etal-EJOC-2015-One-pot-synthesis-crystalization-and-deracemization-of-isoindolinonesAccepted author manuscript, 371 KB

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