Total spontaneous resolution by deracemization of isoindolinones

Fumitoshi Yagishita; Hiroki Ishikawa; Tatsuo Onuki; Shoko Hachiya; Takashi Mino; Masami Sakamoto

doi:10.1002/anie.201205097

Total spontaneous resolution by deracemization of isoindolinones

Angew Chem Int Ed Engl. 2012 Dec 21;51(52):13023-5. doi: 10.1002/anie.201205097. Epub 2012 Nov 13.

Authors

Fumitoshi Yagishita¹, Hiroki Ishikawa, Tatsuo Onuki, Shoko Hachiya, Takashi Mino, Masami Sakamoto

Affiliation

¹ Department of Applied Chemistry and Biotechnology, Graduate School of Engineering, Chiba University, Yayoi-cho, Inage-ku, Japan.

PMID: 23150288
DOI: 10.1002/anie.201205097

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.