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Fe(BF4)2 catalyzed inter- and intramolecular carbonyl-ene reaction of trifluoropyruvate

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Inter- and intramolecular carbonyl-ene reactions have been developed using 5 mol% Fe(BF 4 ) 2 as catalyst, affording homoallylic alcohols in 36–87% isolated yields. This catalyst, prepared from FeCl 2… Click to show full abstract

Inter- and intramolecular carbonyl-ene reactions have been developed using 5 mol% Fe(BF 4 ) 2 as catalyst, affording homoallylic alcohols in 36–87% isolated yields. This catalyst, prepared from FeCl 2 and AgBF 4 , is the first Fe II Lewis acid reported for the carbonyl-ene reaction using ethyl trifluoropyruvate. The method was successfully applied to the reaction of various 1,1-disubstituted alkenes with ethyl trifluoropyruvate and to the cyclization of citronellal.

Keywords: carbonyl ene; intramolecular carbonyl; ene; ene reaction; inter intramolecular

Journal Title: Synlett
Year Published: 2017

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