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Rh-Catalyzed Chemoselective [4 + 1] Cycloaddition Reaction toward Diverse 4-Methyleneprolines

Wangshui Cai, Junxian Wu, Haowei Zhang, Hitesh B. Jalani, Guigen Li*, Hongjian Lu*

*Institute of Chemistry & BioMedical Sciences, Nanjing University, Nanjing 210023, China, Email: guigenlinju.edu.cn, hongjianlunju.edu.cn

W. Cai, J. Wu, H. Zhang, H. B. Jalani, G. Li, H. Lu, J. Org. Chem., 2019, 84, 10877-10891.

DOI: 10.1021/acs.joc.9b01466 (free Supporting Information)



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Abstract

A Rh-catalyzed [4 + 1] cycloaddition of 3-methyleneazetidines to diazo compounds provides 4-methyleneproline derivatives under very mild conditions with a high degree of chemoselectivity. This method can incorporate the proline ester scaffold in pharmaceuticals and natural products. An intramolecular version of the reaction effectively provides proline-fused tricyclic heterocycles.

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Key Words

pyrrolidines


ID: J42-Y2019