Synthesis, absolute configuration, and application of enantiopure trans-1-aminobenz[f]indan-2-ol

Yuka Kobayashi, Kazushi Kinbara, Masaaki Sato, Kazuhiko Saigo

Research output: Contribution to journalArticlepeer-review

13 Citations (Scopus)

Abstract

Both novel enantiopure trans-1-aminobenz[f]indan-2-ols (4) were obtained from the racemate by the diastereomeric salt formation with (+)- and (-)-dibenzoyltartaric acids (8), respectively, and the absolute configuration of the enantiomer 4 in the less-soluble diastereomeric salt of racemic 4 with (+)-8 was determined to be (1S,2S) by an X-ray crystallographic analysis. The chiral recognition ability of the enantiopure amino alcohol was examined for the enantioseparation of racemic 2-arylalkanoic acids by the diastereomeric salt formation. The role of the naphthylene group of the amino alcohol was found to be closely associated with the stabilization of the crystal by CH/π interactions on the basis of an X-ray crystallographic study.

Original languageEnglish
Pages (from-to)108-112
Number of pages5
JournalChirality
Volume17
Issue number2
DOIs
Publication statusPublished - 2005 Feb 14

Keywords

  • 2-arylalkanoic acid
  • Crystal engineering
  • Diastereomeric salt
  • Enantiopure amino alcohol
  • Enantioseparation

ASJC Scopus subject areas

  • Analytical Chemistry
  • Catalysis
  • Pharmacology
  • Drug Discovery
  • Spectroscopy
  • Organic Chemistry

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