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

Yuka Kobayashi, Toshie Kurasawa, Kazushi Kinbara, Kazuhiko Saigo

Research output: Contribution to journalArticle

31 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)7436-7441
Number of pages6
JournalJournal of Organic Chemistry
Volume69
Issue number22
DOIs
Publication statusPublished - 2004 Oct 29

ASJC Scopus subject areas

  • Organic Chemistry

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