Diastereoselective three-component 1,3-dipolar cycloaddition: concise synthesis of functionalized
Yongchao Wang1, Lihua Zheng1, Rongmei Zi1
1Yunnan Key Laboratory of Modern Separation Analysis and Substance Transformation, College of Chemistry and Chemical Engineering, Yunnan Normal University, Kunming 650500, Yunnan Province, P.R. China. ycwang@ynnu.edu.cn.
Abstract:
A novel diastereoselective and regioselective three-component 1,3-dipolar cycloaddition for the concise synthesis of functionalized tetrahydrocarboline-containing spirooxindoles is reported. Diverse 5-(2-nitroaryl)-2,4-dienones were ingeniously employed as dipolarophiles in 1,3-dipolar cycloaddition, affording two types of isomerized tetrahydrocarboline-fused spirooxindoles in 61-93% yields with excellent diastereoselectivities (up to >99 : 1 dr). This reaction not only expands the scope of dipolarophiles in 1,3-dipolar cycloadditions but also enhances the structural and functional diversity of spirooxindoles.
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