Enantioseparation of 1-(p-bromophenyl)ethanol by crystallization of host–guest complexes with permethylated β-cyclodextrin: crystal structures and mechanisms of chiral recognition

✍ Scribed by Arnaud Grandeury; Samuel Petit; Géraldine Gouhier; Valérie Agasse; Gérard Coquerel

• Publisher: Elsevier Science
• Year: 2003
• Tongue: English
• Weight: 703 KB
• Volume: 14
• Category: Article
• ISSN: 0957-4166
• DOI: 10.1016/s0957-4166(03)00360-4

✦ Synopsis

It is shown that racemic 1-(p-bromophenyl)ethanol (p-Br-PE) can be quantitatively resolved by successive recrystallizations of (1:1) supramolecular complexes formed with permethylated b-cyclodextrin (TMb-CD). The two enantiomerically pure complexes were characterized by physical methods and their crystal structures were determined. The comparison of both inclusion geometries and packing modes in these structures revealed distinct structural features allowing the enantioseparation of the guest to be understood. Chiral discrimination mechanisms are discussed in terms of the capability of TMb-CD to induce the formation of stereospecific host-guest complexes by simple crystallization in aqueous medium.