Fumitoshi Yagishita, Hiroki Ishikawa, Tatsuo Onuki, Shoko Hachiya, Prof. Takashi Mino and Prof. Masami Sakamoto Total Spontaneous Resolution by Deracemization of Isoindolinones Angewandte Chemie International Edition 51
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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