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Stereoselective Synthesis of 3-Carboxy-4,5-dihydropyrroles via an Intramolecular Iminium Ion Cyclization Reaction

Jinbao Xiang, Hongxiang Xie, Zhuo Li, Qun Dang and Xu Bai*

*The School of Pharmaceutical Sciences and The College of Chemistry, Jilin University, 1266 Fujin Road, Changchun, Jilin 130021, P. R. China, Email:

J. Yiang, H. Xie, Z. Li, Q. Dang, X. Bai, Org. Lett., 2015, 17, 3810-3813.

DOI: 10.1021/acs.orglett.5b01787

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An intramolecular iminium ion cyclization reaction of readily accessible Baylis-Hillman derivatives and aldehydes enables a synthesis of trans-4,5-disubstituted 3-carboxy-4,5-dihydropyrroles in good yield. These dihydropyrroles can easily be converted to pyrroles or pyrrolidines.

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ID: J54-Y2015