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A novel synthesis of 4-alkyl-4-(4-methoxyphenyl)cyclohex-2-en-1-ones and the Sceletium alkaloid,o-methyljoubertiamine.
Affiliation:1. Institut für Festkörperphysik, Technische Universität Berlin, Hardenbergstraße 36, 10623, Berlin, Germany;2. Department Physik, Friedrich-Alexander-Universität Erlangen-Nürnberg, Staudtstraße 7, 91058, Erlangen, Germany;3. Institute of Organic Chemistry, Justus Liebig University, Heinrich-Buff-Ring 17 and Center for Materials (LaMa) Justus Liebig University, Heinrich-Buff-Ring 16, 35392, Giessen, Germany;4. Department of Organic Chemistry, Kiev Polytechnic Institute, pr. Pobedy 37, 03056, Kiev, Ukraine
Abstract:The dianion formed by reduction of (η66-4,4′-dimethoxybiphenyl)[Cr(CO)3]2 reacts with electrophiles such as methyl or ethyl triflate or allyl tosylate at −78 °C followed by CF3CO2H and I2 to form 4-alkyl-4-(4-methoxyphenyl)cyclohex-2-en-1-ones.
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