Multicomponent Domino Synthesis of Cyclopenta[ b ]furan-2-ones

RIVEIRA, M. J.; RIVEIRA, M. J.; LA-VENIA, A.; LA-VENIA, A.; MARCARINO, M. O.; MARCARINO, M. O.

ORGANIC LETTERS

AMER CHEMICAL SOC

Año: 2018 vol. 20 p. 4000 - 4004

1523-7060

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.