Department of Medicinal Chemistry (Tsunoda Lab.)

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Eur. J. Org. Chem 2013, 36, 8208-8213 (2013).

A Method to Prepare Optically Active Acyclic α-Benzyl Ketones by Thermodynamically Controlled Deracemization

Kaku, H., Imai, T., Kondo, R., Mamba, S., Watanabe, Y., Inai, M., Nishii, T., Horikawa, M., Tsunoda, T.

Thermodynamically controlled deracemization of some acyclic ketones bearing a chiral center at the position α to the carbonyl group was satisfactorily achieved. Acyclic ketones with high optical purities could be isolated after treatment of the racemic ketones with base in aqueous MeOH in the presence of (–)-(2R,3R)-trans-2,3-bis(hydroxydiphenylmethyl)-1,4-dioxaspiro[5.4]decane (1a). The efficiency of the deracemization was appreciably influenced by the ratio of H2O/MeOH used as solvent.