Dynamic chirality of (E)-5-cyclononen-1-one and its enolate

Katsuhiko Tomooka, Takayuki Ezawa, Hiroko Inoue, Kazuhiro Uehara, Kazunobu Igawa

Research output: Contribution to journalArticle

17 Citations (Scopus)

Abstract

It has been found that (E)-5-cyclononen-1-one (2a) exhibits marginal planar chirality owing to an insufficient topological constraint, whereas the enolates 3 derived from 2a show robust planar chirality. Enantioenriched enolates are easily prepared by enzymatic hydrolysis, and they show an ability to serve as chiral nucleophiles.

Original languageEnglish
Pages (from-to)1754-1756
Number of pages3
JournalJournal of the American Chemical Society
Volume133
Issue number6
DOIs
Publication statusPublished - Feb 16 2011

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Chirality
Hydrolysis
Nucleophiles
Enzymatic hydrolysis

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

Dynamic chirality of (E)-5-cyclononen-1-one and its enolate. / Tomooka, Katsuhiko; Ezawa, Takayuki; Inoue, Hiroko; Uehara, Kazuhiro; Igawa, Kazunobu.

In: Journal of the American Chemical Society, Vol. 133, No. 6, 16.02.2011, p. 1754-1756.

Research output: Contribution to journalArticle

Tomooka, Katsuhiko ; Ezawa, Takayuki ; Inoue, Hiroko ; Uehara, Kazuhiro ; Igawa, Kazunobu. / Dynamic chirality of (E)-5-cyclononen-1-one and its enolate. In: Journal of the American Chemical Society. 2011 ; Vol. 133, No. 6. pp. 1754-1756.
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