272766-97-9Relevant 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.
