Citation: Tanglin Liu, Qinghua Li, Zhaolin He, Jiawei Zhang, Chunjiang Wang. Catalytic asymmetric construction of spiro pyrrolidines with contiguous quaternary centers via 1,3-dipolar cycloaddition of azomethine ylides[J]. Chinese Journal of Catalysis, ;2015, 36(1): 68-77. doi: 10.1016/S1872-2067(14)60204-7 shu

Catalytic asymmetric construction of spiro pyrrolidines with contiguous quaternary centers via 1,3-dipolar cycloaddition of azomethine ylides

1.
a College of Chemistry and Molecular Sciences, Wuhan University, Wuhan 430072, Hubei, China;

Corresponding author: Chunjiang Wang,
Received Date: 26 June 2014
Available Online: 22 July 2014
Fund Project: 国家重点基础研究发展计划(973计划, 2011CB808600) (973计划, 2011CB808600) 国家自然科学基金(21172176, 21372180) (21172176, 21372180) 湖北省高等学校科研基金资助项目(ZRZ0273) (ZRZ0273) 教育部博士学术新人奖(5052011203011). (5052011203011)

Bioactive 5-aza-spiro[2,4]heptanes with high functionality and up to three contiguous all-carbon quaternary stereogenic centers were synthesized by Cu(I)-catalyzed asymmetric endo-selective 1,3-dipolar cycloaddition of azomethine ylides with cyclopropylidene acetates. This synthesis system performs well for a broad scope of substrates. α-unsubstituted/α-substituted azomethine ylides and cyclopropylidene acetates are compatible 1,3-dipoles and dipolarophiles, which afford the spiro heterocycles with contiguous quaternary centers at 2-, 3- and 4-positions of the pyrrolidine ring in good yield (up to 97%) and high diastereoselectivity (95:5->98:2 d.r) and excellent enantioselectivity (87%-98% ee).
- Asymmetric catalysis,
- Quaternary stereogenic center,
- 1,3-Dipolar cycloaddition,
- Azomethine ylide,
- Cyclopropylidene acetate,
- 5-Aza-spiro[2,4]heptane
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