Inherently chiral molecular clips: Synthesis, chiroptical properties, and application to chiral discrimination

Gaku Fukuhara, Süreyya Madenci, Jolanta Polkowska, Frank Bastkowski, Frank Gerrit Klärner, Yumi Origane, Masayuki Kaneda, Tadashi Mori, Takehiko Wada, Yoshihisa Inoue

Research output: Contribution to journalArticlepeer-review

20 Citations (Scopus)

Abstract

Inherently chiral molecular clips (MCs). pseudoenantiomeric anti-1 and anti-2, as well as mesoid syn-3, were synthesized by diastereodifferentiating repetitive Diels-Alder reactions of the achiral bisdienophile 6 with chiral diene 5 generated in situ from (-)-menthyl 3,4-bis(dibromomethyl)-benzoate 4. These MCs were success fully separated by chiral HPLC to give optically active anti-1 and anti-2 and almost optically inactive syn-3. The structures of anti-1, anti-2, and syn-3 were assigned by high-resolution NMR and the absolute configurations of anti1 and anti-2 were determined by the exciton-chirality method. Optically active anti-2 can serve as a chiral host. It binds the HCl adduct of D-tryptophan methyl ester (D-TrpOMe·HCl) 3.5 times stronger than the i.-enantiomer (KD/KL = 3.5).

Original languageEnglish
Pages (from-to)2473-2479
Number of pages7
JournalChemistry - A European Journal
Volume13
Issue number9
DOIs
Publication statusPublished - 2007 Jun 26
Externally publishedYes

Keywords

  • Chirality
  • Circular dichroism
  • Exciton coupling
  • Host-guest systems
  • Molecular clips

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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