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

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

doi:10.1021/ja1092375

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

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

Department of Applied Molecular Chemistry

Research output: Contribution to journal › Article › peer-review

25 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 language	English
Pages (from-to)	1754-1756
Number of pages	3
Journal	Journal of the American Chemical Society
Volume	133
Issue number	6
DOIs	https://doi.org/10.1021/ja1092375
Publication status	Published - Feb 16 2011

All Science Journal Classification (ASJC) codes

Catalysis
General Chemistry
Biochemistry
Colloid and Surface Chemistry

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10.1021/ja1092375

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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.",

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AU - Tomooka, Katsuhiko

AU - Ezawa, Takayuki

AU - Inoue, Hiroko

AU - Uehara, Kazuhiro

AU - Igawa, Kazunobu

PY - 2011/2/16

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N2 - 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.

AB - 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.

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M3 - Article

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

Abstract

All Science Journal Classification (ASJC) codes

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