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Total spontaneous resolution by deracemization of isoindolinones. | LitMetric

Total spontaneous resolution by deracemization of isoindolinones.

Angew Chem Int Ed Engl

Department of Applied Chemistry and Biotechnology, Graduate School of Engineering, Chiba University, Yayoi-cho, Inage-ku, Japan.

Published: December 2012

AI Article Synopsis

  • The study focuses on the separation of 3-hydroxy-3-phenylisoindolin-1-ones using a method called dynamic preferential crystallization.
  • These compounds can be racemized by undergoing ring-opening and ring-closing reactions with achiral intermediates in basic conditions.
  • By crystallizing from a toluene solution with DBU and using stirring and solvent evaporation, the researchers successfully produced optically active crystals with high enantiomeric excess (ee) values.

Article Abstract

Separated: 3-hydroxy-3-phenylisoindolin-1-ones have been resolved by dynamic preferential crystallization. The compounds were effectively racemized through ring-opening and ring-closing reactions via achiral intermediates under basic conditions. Crystallization from a toluene solution containing 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) with stirring and evaporation of the solvent gave optically active crystals quantitatively with high ee values.

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Source
http://dx.doi.org/10.1002/anie.201205097DOI Listing

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