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

Authors :: Tomooka, Katsuhiko
Ezawa, Takayuki
Inoue, Hiroko
Uehara, Kazuhiro
Igawa, Kazunobu
Source :: Journal of the American Chemical Society. 2/16/2011, Vol. 133 Issue 6, p1754-1756. 3p.
Publication Year :: 2011
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. [ABSTRACT FROM AUTHOR]