溶媒による立体制御を利用したジアステレオマー塩法による光学分割法の開発《マイレビュー》
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概要
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Solvent-induced chirality control in the enantioseparation of 1-phenylethylamine 1 by N-(p-toluenesulfonyl)-(S)-phenylalanine 2 via diastereomeric salt formation was studied. (S)-1·(S)-2 salt was preferentially crystallized as a less-soluble salt from aqueous alcohol, while (R)-1·(S)-2 salt was mainly obtained by addition of solvents with a six-membered ring such as 1,4-dioxane, cyclohexane, tetrahydropyran and cyclohexene to 2-propanol. Further investigations were carried out from the viewpoints of molecular structures and X-raycrystallographic analyses. Crystallographic analyses have revealed that incorporation of the six-membered ring solvent molecule in (R)-1·(S)-2 without hydrogen bonds changed the molecular conformation of (S)-2 to stabilize the salt, which changed the selectivity of 1 in the enantioseparation.