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Published on: September 21, 2019
Multicomponent Domino Synthesis of Cyclopenta[ b]furan-2-ones
Martín J Riveira1, Maribel O Marcarino1, Agustina La-Venia1
1Instituto de Química Rosario , Facultad de Ciencias Bioquímicas y Farmacéuticas, Universidad Nacional de Rosario-CONICET , Suipacha 531 , S2002LRK Rosario , Argentina.
Abstract:
A stereoselective multicomponent reaction involving Meldrum's acid, a conjugated dienal, and an alcohol is reported. Valuable cyclopenta[ b]furan-2-ones are obtained as products of this straightforward transformation, which is accompanied by the formation of four stereocenters, two new cycles, and four new bonds (two C-C and two C-heteroatom). A reaction mechanism was elaborated involving an initial Knoevenagel condensation followed by cycloisomerization and eventual fragmentation.
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