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  • Title: Rational design of CH/pi interaction sites in a basic resolving agent.
    Author: Kobayashi Y, Kurasawa T, Kinbara K, Saigo K.
    Journal: J Org Chem; 2004 Oct 29; 69(22):7436-41. PubMed ID: 15497967.
    Abstract:
    A novel synthetic basic resolving agent, cis-1-aminobenz[f]indan-2-ol (ABI), was rationally designed by introducing effective CH/pi interaction sites to cis-1-aminoindan-2-ol (AI), whose chiral recognition ability has been reported from our laboratory. ABI was applicable to a wide variety of racemic arylalkanoic acids and showed moderate to excellent chiral recognition ability, which was obviously higher than that of AI. The fundamental and important role of CH/pi interactions, such as tunable CH(sp(2))/pi and CH(sp(3))/pi interactions, in the chiral recognition by ABI was revealed by X-ray crystallographic study.
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