Rational design of CH/π interaction sites in a basic resolving agent

Article abstract of DOI:10.1021/jo049154d

A novel synthetic basic resolving agent, cis-1-aminobenz[f]indan-2-ol (ABI), was rationally designed by introducing effective CH/π 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/π interactions, such as tunable CH(sp²)/π and CH(sp ³)/π interactions, in the chiral recognition by ABI was revealed by X-ray crystallographic study.