Preparation of optically active ketones from equilibrium systems using highly selective chiral molecular recognition.

2016 Fiscal Year Final Research Report

• Project/Area Number: 26460027
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Multi-year Fund
• Section: 一般
• Research Field: Chemical pharmacy
• Research Institution: Tokushima Bunri University
• Principal Investigator: KAKU HIROTO 徳島文理大学, 薬学部, 准教授 (90299339)
• Project Period (FY): 2014-04-01 – 2017-03-31
• Keywords: 平衡複雑系 / 不斉分子認識 / デラセミ化 / ホスト-ゲスト化学 / TADDOL型ホスト分子

Outline of Final Research Achievements

trans-cis mixture of (5R)-2-benzyl-5-methylcyclohexanone were converted to cis-form (91% de) by a thermodynamic equilibrium condition using TADDOL-type host molecule 1 in alkaline aqueous MeOH. The efficiency of this conversion was strongly influenced by the ratio of the solvent components (H2O/MeOH). Cyclohexenone was converted to (S)-3-methoxycyclohexanone using TADDOL-type host molecule 1 and DBU as a basic catalyst in H2O/MeOH (3:7). X-ray analytical studies were also carried out and disclosed the nature of this chiral molecular recognition process in the solid phase.

Free Research Field

化学系薬学