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

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...

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Bibliographic Details
Published in:Organic letters 2018-07, Vol.20 (13), p.4000-4004
Main Authors: Riveira, Martín J, Marcarino, Maribel O, La-Venia, Agustina
Format: Article
Language:English
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.8b01567