Diastereoselective construction of spirocyclic pyrrolidines bearing two quaternary centers via Cu^II-P, N-Ligand catalyzed 1,3-dipolar cycloaddition

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• 作者：Li-Wei Tang^a ; Chuan Li^a ; Bao-Jing Zhao^a ; Li Lan^a ; Man Zhang^a ; Zhi-Ming Zhou^a ; ^b ; ^{zzm@bit.edu.cn}
• 关键词：Spiropyrrolidine ; Quaternary center ; 1 ; 3-Dipolar cycloaddition ; Spirolactone
• 刊名：Tetrahedron
• 出版年：2017
• 出版时间：16 February 2017
• 年：2017
• 卷：73
• 期：7
• 页码：923-930
• 全文大小：740 K
• 卷排序：73

文摘

Here, we report a convenient access to diastereoselective synthesis of polysubstituted pyrrolidines bearing a unique spiro quaternary center at the C-2 position and another quaternary center at C-4. The synthesis system, CuII/P, N-Ligand-catalyzed 1, 3-dipolar cycloaddition, by employing homoserine lactone derived cyclic imino esters as the dipoles and α, α, β-trisubstituted olefins as the dipolarophlies, provides exo-spiro-pyrrolidines with good yields, high diastereoselectivities (up to >98:2 dr) and performs well for a broad scope of substrates.