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

研究成果: Article査読

20 被引用数 (Scopus)

抄録

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).

本文言語English
ページ(範囲)2473-2479
ページ数7
ジャーナルChemistry - A European Journal
13
9
DOI
出版ステータスPublished - 2007
外部発表はい

ASJC Scopus subject areas

  • 触媒
  • 有機化学

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