- Introducing a new radical trifluoromethylation reagent
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Perfluoro-3-ethyl-2,4-dimethyl-3-pentyl radical (PPFR) is a persistent radical stable at room temperature, but easily decomposes at 90 °C to produce a CF3 radical which is able to react with a variety of aromatic compounds to afford the corresponding trifluoromethyl derivatives, usually as mixtures of regioisomers in good to excellent overall yields.
- Sato, Azusa,Han, Jianlin,Ono, Taizo,Wzorek, Alicja,Ace?a, José Luis,Soloshonok, Vadim A.
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supporting information
p. 5967 - 5970
(2015/03/30)
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- Asymmetric syntheses of (S)-Fenfluramine using Sharpless Epoxidation Methods
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We describe one synthesis of (S)-fenfluramine and several syntheses of its precursors (R)- and (S)-1-(meta-trifluoromethylphenyl)propan-2-ols.They were obtained from the asymmetric epoxidation of the primary allylic alcohol 5 and from the kinetic resolution with asymmetric epoxidation of teh secondary allylic alcohol 6.
- Goument, Bertrand,Duhamel, Lucette,Mauge, Robert
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p. 171 - 188
(2007/10/02)
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- Epoxides, amino alcohols, and aziridines as key intermediates in the asymmetric synthesis of (S)-fenfluramine
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The epoxides 3E, 3Z and 8 were obtained from the isomeric alkenes 2E, 2Z and 7.The epoxides were ring-opened by ethylamine in ethanol yielding mixtures of the amino alcohols 4E and 11E, 4T and 11T, and 9, respectively, which were transformed into the aziridines 5trans, 5cis and 12.The regiospecific Pd/C-catalyzed reduction of these aziridines gave fenfluramine 1.The three epoxides 3trans, 3cis and 8 were reduced regiospecifically into 1-propan-2-ol 6, a potent precursor to fenfluramine 1.The validity of our method for asymmettric synthesis has been demonstrated by a synthesis of (S)-fenfluramine 1 starting from the amino alcohol (S)-9.Keyword - fenfluramine / asymmetric synthesis / epoxide / amino alcohol / aziridine / regiospecific catalytic hydrogenation / 1-propan-2-ols
- Goument, B.,Duhamel, L.,Mauge, R.
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p. 459 - 466
(2007/10/02)
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