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Access to Multisubstituted Furan-3-carbothioates via Cascade Annulation of α-Oxo Ketene Dithioacetals with Isoindoline-1,3-dione-Derived Propargyl Alcohols
- Source :
- The Journal of organic chemistry. 83(15)
- Publication Year :
- 2018
-
Abstract
- A Bronsted acid-promoted, unprecedented formal (3 + 2) annulation strategy for the synthesis of multisubstituted furan-3-carbothioates is reported. This transformation represents the first regioselective annulation of α-oxo ketene dithio-acetals as 1,3-bis-nucleophiles in a cascade manner. The choice of isoindoline-1,3-dione-derived propargyl alcohols is crucial to the uncommon annulation mode between an alkyne-type bis-electrophile and a 1,3-bis-nucleophile under metal-free conditions. The scale-up of the synthesis and several interesting transformations of an as-synthesized product were further investigated. A Nazarov-like cyclization is proposed for the ring-closure process according to the experimental observations.
Details
- ISSN :
- 15206904
- Volume :
- 83
- Issue :
- 15
- Database :
- OpenAIRE
- Journal :
- The Journal of organic chemistry
- Accession number :
- edsair.doi.dedup.....f32b29dfe3fbb551aa43bbd73861a38a