69153-92-0Relevant academic research and scientific papers
Enantioselective synthesis of functionalised decalones by robinson annulation of substituted cyclohexanones, derived from R-(-)-carvone
Jansen, Ben J. M.,Hendrikx, Cindy C. J.,Masalov, Nikolai,Stork, Gerrit A.,Meulemans, Tommi M.,Macaev, Fliur Z.,De Groot, Aede
, p. 2075 - 2094 (2007/10/03)
The copper catalysed conjugate addition of methyl magnesium iodide to cyclohexenones and trapping of the enolate as its trimethylsilyl enol ether, followed by a trityl hexachloroantimonate (TrSbCl6) catalysed Mukaiyama- reaction, was applied to R-(-)-carvone. This proved to be an efficient method for the preparation of C-2, C-3 functionalised chiral cyclohexanones. These compounds were converted into their α-cyano ketones, which were submitted to Robinson annulation reactions with methyl vinyl ketone. The scope and limitations of these annulations were investigated. A series of highly functionalised chiral decalones were obtained that can be used as starting compounds in the total syntheses of enantiomerically pure clerodanes. (C) 2000 Elsevier Science Ltd.
Optical rotatory dispersion studies. 132. Conformational isotope effect in deuterium-substituted cyclohexanones
Lee, Shy-Fuh,Barth, Guenter,Djerassi, Carl
, p. 295 - 301 (2007/10/02)
The observed temperture dependence of the circular dichroism spectra of (3R)-2,2-dimethyl-3-deuteriocyclohexanone (1), (4S)-2,2-dimethyl-4-deuteriocyclohexanone (2), and (5S)-2,2-dimethyl-5-deuteriocyclohexanone (3) is interpreted as reflecting a conforma
