Synthesis of β-(trifluoromethyl)furans and spiro-gem- dichlorocyclopropanes from cyclic 1,3-dicarbonyl compounds and α-(trihaloethylidene)nitroethanes

Abstract

While 1,3-dicarbonyl compounds react with (E)-1,1,1-trifluoro-3-nitrobut-2- ene in the presence of sodium acetate to produce the target β- (trifluoromethyl)furans, their reaction with (E)-1,1,1-trichloro-3-nitrobut-2- ene, under the same conditions, took an entirely different course and gave spiro-gem-dichlorocyclopropanes bearing a 1-nitroethyl moiety, with high diastereoselectivity and in good yields. © 2013 Elsevier Ltd. All rights reserved.