Access to Multisubstituted Furan-3-carbothioates via Cascade Annulation of alpha-Oxo Ketene Dithioacetals with Isoindoline-1,3-dione-Derived Propargyl Alcohols

作者：Bai, Li-Gang; Chen, Ming-Tao; Xiao, Dong-Rong; Zhao, Liu-Bin^*; Luo, Qun-Li^*

来源：Journal of Organic Chemistry, 2018, 83(15): 7648-7658.

DOI：10.1021/acs.joc.8b00401

• BOND-FORMING REACTIONS
• 3+2 CYCLOADDITION
• REGIOSELECTIVE SYNTHESIS
• ORGANIC-SYNTHESIS
• FACILE SYNTHESIS
• GOLD CARBENES
• OXOKETENE DITHIOACETALS
• ALKYNES
• ACID
• ISOCYANIDES

A Bronsted acid-promoted, unprecedented formal (3 + 2) annulation strategy for the synthesis of multisubstituted furan-3carbothioates is reported. This transformation represents the first regioselective annulation of alpha-oxo ketene dithio-acetals as 1,3-bisnucleophiles 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.

• 出版日期2018-8-3
• 单位西南大学