Chiral discrimination of 2-arylalkanoic acids by (1S,2R)-1-aminoindan-2-ol through the formation of a consistent columnar supramolecular hydrogen-bond network

Kazushi Kinbara, Yuka Kobayashi, Kazuhiko Saigo

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3 Citations (Scopus)

Abstract

Enantiopure cis-1-aminoindan-2-ol was selected as a basic resolving agent for racemic 2-arylalkanoic acids on the basis that its rigid cis-conformation would favor the formation of a supramolecular hydrogen-bonded column, in which chiral discrimination of the racemic carboxylate would occur. It was found that this amino alcohol possesses high resolving efficiency for a variety of racemic acids; also, X-ray crystallographic analyses of the diastereomeric salts showed that a columnar hydrogen-bond network is formed in both the less- and more-soluble diastereomeric salts, as we had expected. A detailed study on the stabilising interactions suggested that there are two that play an important role: (i) hydrogen bonding between the ammonium and hydroxy groups and the acid carboxylate, which determines the formation of the columnar network and (ii) CH⋯π, which influences the herringbone packing of the aromatic groups, implying that it also plays some role in chiral discrimination.

Original languageEnglish
Pages (from-to)111-119
Number of pages9
JournalJournal of the Chemical Society. Perkin Transactions 2
Issue number1
Publication statusPublished - 2001 Dec 1

ASJC Scopus subject areas

  • Chemistry(all)

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