Dynamic Chirality of (E)-5-Cyclononen-1-one and its Enolate

K Tomooka, T Ezawa, H Inoue, K Uehara…

Index: Tomooka, Katsuhiko; Ezawa, Takayuki; Inoue, Hiroko; Uehara, Kazuhiro; Igawa, Kazunobu Journal of the American Chemical Society, 2011 , vol. 133, # 6 p. 1754 - 1756

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Citation Number: 15

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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