Substrate-Controlled Pd-Catalyzed Divergent Decarboxylative Cycloaddition of Vinyloxazolidine-2,4-Diones with Azadienes for the Construction of Spirocycles and Medium-Sized Heterocycles
Shi-Ting Xie , Zhen-Hua Wang , Lei Yang , Jian-Qiang Zhao , Yong You , Yan-Ping Zhang , Wei-Cheng Yuan
Chinese Journal of Chemistry ›› 2025, Vol. 43 ›› Issue (18) : 2385 -2392.
Substrate-Controlled Pd-Catalyzed Divergent Decarboxylative Cycloaddition of Vinyloxazolidine-2,4-Diones with Azadienes for the Construction of Spirocycles and Medium-Sized Heterocycles
Herein, we report a substrate-controlled palladium-catalyzed divergent decarboxylative cycloaddition of vinyloxazolidine-2,4-diones with azadienes. The reaction of benzofuran-derived azadienes undergoes a decarboxylative (3+2) cycloaddition process to access spiro[benzofuran-butyrolactam] derivatives in good yields with acceptable diastereoselectivities. In contrast, the reaction of benzothiophene-based azadienes proceeds a decarboxylative (5+4) cycloaddition pathway to give benzothieno[1,2-d]diazonin-5-ones in moderate to high yields. Gram-scale synthesis and further transformations demonstrated the potential synthetic utility of the developed protocol.
Palladium catalysis / Decarboxylative cycloaddition / Vinyloxazolidine-2,4-diones / Azadienes / Spirocycles / Medium-sized heterocycles
2025 SIOC, CAS, Shanghai, & WILEY-VCH GmbH
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