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

18 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
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

Access to Document

10.1021/ja1092375

Fingerprint Dive into the research topics of 'Dynamic chirality of (E)-5-cyclononen-1-one and its enolate'. Together they form a unique fingerprint.

Cite this

Tomooka, K., Ezawa, T., Inoue, H., Uehara, K., & Igawa, K. (2011). Dynamic chirality of (E)-5-cyclononen-1-one and its enolate. Journal of the American Chemical Society, 133(6), 1754-1756. https://doi.org/10.1021/ja1092375

@article{e7fb3ea54488481abc7f818fe1f8da9d,

title = "Dynamic chirality of (E)-5-cyclononen-1-one and its enolate",

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.",

author = "Katsuhiko Tomooka and Takayuki Ezawa and Hiroko Inoue and Kazuhiro Uehara and Kazunobu Igawa",

year = "2011",

month = feb,

day = "16",

doi = "10.1021/ja1092375",

language = "English",

volume = "133",

pages = "1754--1756",

journal = "Journal of the American Chemical Society",

issn = "0002-7863",

publisher = "American Chemical Society",

number = "6",

}

TY - JOUR

T1 - Dynamic chirality of (E)-5-cyclononen-1-one and its enolate

AU - Tomooka, Katsuhiko

AU - Ezawa, Takayuki

AU - Inoue, Hiroko

AU - Uehara, Kazuhiro

AU - Igawa, Kazunobu

PY - 2011/2/16

Y1 - 2011/2/16

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.

UR - http://www.scopus.com/inward/record.url?scp=79951520359&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=79951520359&partnerID=8YFLogxK

U2 - 10.1021/ja1092375

DO - 10.1021/ja1092375

M3 - Article

C2 - 21265519

AN - SCOPUS:79951520359

VL - 133

SP - 1754

EP - 1756

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

SN - 0002-7863

IS - 6

ER -