149209-56-3Relevant academic research and scientific papers
Preparation of Optically Active Cyclohexenones: Chirons for the Lipophilic Moiety of Flowery- and Woody-like Odorant Ketones
Chapuis, Christian,Brauchli, Robert,Thommen, Walter
, p. 535 - 544 (2007/10/02)
Optically active 2,5,6,6- and 2,4,4,5-tetralkylcyclohex-2-en-1-ones ((+)-2a-d and (-)-5a-d), important building blocks for flowery- and woody-like odorants, have been prepared.Compounds (+)-2a-d and (-)-5a-d were obtained by ozonolysis of the correspondin
Preparation of Optically Active Flowery and Woody-Like Odorant Ketones via Corey-Chaykovsky Oxiranylation: Irones and Analogues
Chapuis, Christian,Brauchli, Robert
, p. 2070 - 2088 (2007/10/02)
α-, β-, and γ-Irones and analogues have been prepared from optically active (+)-1, (+)-6a,b, and (+)-17, via a Corey-Chaykovsky oxiranylation (Me2S, Me2SO4, Me2SO, NaOH) followed by isomerisation (SnCl4 or MgBr2). (+)-Dihydrocyclocitral (19a), obtained from (-)-citronellal, and analogue (+)-19b, were condensed with various ketones to afford (+)-21a-f, and after hydrogenation (+)-22a-f.A mild oxidative degradation of aldehydes (+)-trans- and (-)-cis-8a,b to ketones (-)-16a,b, as well as olfactive evaluations, 13C-NMR assignments, and absolute configurations of the intermediate epoxides, aldehydes, and alcohols are presented.
