Crystallization-based optical resolution of 1,1′-binaphthalene-2,2′-dicarboxylic acid via 1-phenylethylamides: control by the molecular structure and dielectric property of solvent

Yuki Kato, Yuichi Kitamoto, Naoya Morohashi, Yosuke Kuruma, Shuichi Oi, Kenichi Sakai, Tetsutaro Hattori

Research output: Contribution to journalArticlepeer-review

10 Citations (Scopus)

Abstract

In the recrystallization of a diastereomeric mixture of amides (RSa,S)-1 formed from racemic 1,1′-binaphthalene-2,2′-dicarboxylic acid and (S)-1-phenylethylamine, either of the diastereomers crystallizes out as a diastereomerically pure form, depending on the solvent employed; sterically undemanding solvents, acetone, dichloromethane, and acetonitrile, afford crystals formulated as (Sa,S)-1·solvent with an exception of ethanol, which affords (Ra,S)-1·EtOH, while sterically bulkier solvents afford (Ra,S)-1 including no solvent. The stereoselectivity can be rationalized by the crystal structures. A dielectrically controlled resolution (DCR) can also be carried out by using mixed solvents, which contain, for example, 25 vol % of acetone and varying ratios of hexane and 1-propanol in total 75 vol %; (Sa,S)-1·acetone is deposited as crystals from the solvents with a dielectric constant (ε) range 8.9 ≤ ε ≤ 10.2, while (Ra,S)-1 is deposited from the solvents with 14.8 ≤ ε ≤ 20.3.

Original languageEnglish
Pages (from-to)1998-2002
Number of pages5
JournalTetrahedron Letters
Volume50
Issue number17
DOIs
Publication statusPublished - 2009 Apr 29

Keywords

  • 1,1′-Binaphthalene-2,2′-dicarboxylic acid
  • 1-Phenylethylamine
  • Dielectrically controlled resolution (DCR)
  • Solvent-controlled resolution

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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