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Regioselective 1,4-trifluoromethylation of α,β-enones using ‘protect-in-situ’ methodology
Authors:Dmitri V Sevenard  Vyacheslav Ya SosnovskikhAlexander A Kolomeitsev  Martin H KönigsmannGerd-Volker Röschenthaler
Affiliation:a Institute of Inorganic & Physical Chemistry, University of Bremen, Leobener Strasse, 28334 Bremen, Germany
b Department of Chemistry, Ural State University, Lenina 51, 620083 Ekaterinburg, Russia
c Institute of Organic Chemistry, Murmanskaya 5, 02094 Kiev, Ukraine
Abstract:In a convenient and efficient procedure, the nucleophilic 1,4-trifluoromethylation of several α,β-enones using (trifluoromethyl)trimethylsilane was achieved. The high regioselectivity of the reaction has been reached by blocking the carbonyl moiety of the electrophile with a bulky aluminum-centered Lewis acid.
Keywords:nucleophilic addition  (trifluoromethyl)trimethylsilane  trifluoromethylation  regioselectivity
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