Solvent-induced chirality control in the enantioseparation of 1-phenylethylamine via diastereomeric salt formation
✍ Scribed by Koichi Kodama; Yuria Kimura; Hiroaki Shitara; Mikio Yasutake; Rumiko Sakurai; Takuji Hirose
- Publisher
- John Wiley and Sons
- Year
- 2010
- Tongue
- English
- Weight
- 929 KB
- Volume
- 23
- Category
- Article
- ISSN
- 0899-0042
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✦ Synopsis
Abstract
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 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 dioxane, cyclohexane, tetrahydropyran, and cyclohexene to 2‐propanol. Further investigations were carried out from the viewpoints of molecular structures, optical rotation measurement, and X‐ray crystallographic 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. Chirality, 2011. © 2010 Wiley‐Liss, Inc.