Tuning the chiral cavity of macrocyclic receptor for chiral recognition and discrimination

Tadashi Ema, Daisuke Tanida, Kazuki Hamada, Takashi Sakai

Research output: Contribution to journalArticle

42 Citations (Scopus)

Abstract

(Chemical Equation Presented) The size and shape of the chiral cavity of a macrocyclic receptor were tuned by the alteration of the binaphthyl moiety to improve the chiral recognition/discrimination ability. For example, host 3 with the 3,5-bis(trifluoromethyl)phenyl group at the 3,3′-positions showed improved enantioselectivity for small molecules such as 2-chloropropionic acid and methyl lactate as evaluated by the binding constants. This host 3 also had an excellent ability as an NMR chiral solvating agent.

Original languageEnglish
Pages (from-to)9129-9132
Number of pages4
JournalJournal of Organic Chemistry
Volume73
Issue number22
DOIs
Publication statusPublished - Nov 21 2008

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Enantioselectivity
Tuning
Nuclear magnetic resonance
Molecules
methyl lactate
2-chloropropionic acid

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Tuning the chiral cavity of macrocyclic receptor for chiral recognition and discrimination. / Ema, Tadashi; Tanida, Daisuke; Hamada, Kazuki; Sakai, Takashi.

In: Journal of Organic Chemistry, Vol. 73, No. 22, 21.11.2008, p. 9129-9132.

Research output: Contribution to journalArticle

Ema, Tadashi ; Tanida, Daisuke ; Hamada, Kazuki ; Sakai, Takashi. / Tuning the chiral cavity of macrocyclic receptor for chiral recognition and discrimination. In: Journal of Organic Chemistry. 2008 ; Vol. 73, No. 22. pp. 9129-9132.
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