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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

Version of Record online: 13 NOV 2012 | DOI: 10.1002/anie.201205097

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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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