This work was supported by Grants-in-Aid for Scientific Research (Nos. 21350024, 22655012) from the Ministry of Education, Culture, Sports, Science and Technology (MEXT) of the Japanese Government.
Total Spontaneous Resolution by Deracemization of Isoindolinones†
Article first published online: 13 NOV 2012
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 51, Issue 52, pages 13023–13025, December 21, 2012
How to Cite
Yagishita, F., Ishikawa, H., Onuki, T., Hachiya, S., Mino, T. and Sakamoto, M. (2012), Total Spontaneous Resolution by Deracemization of Isoindolinones . Angew. Chem. Int. Ed., 51: 13023–13025. doi: 10.1002/anie.201205097
- Issue published online: 18 DEC 2012
- Article first published online: 13 NOV 2012
- Manuscript Revised: 29 OCT 2012
- Manuscript Received: 29 JUN 2012
- Ministry of Education, Culture, Sports, Science and Technology (MEXT)
- chiral resolution;
- preferential crystallization
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.