Iodine-Promoted Formal [3+2] Cycloaddition of Enaminone: Access to 2-Hydroxy-1,2-dihydro-pyrrol-3-ones with Quaternary Carbon Center
Xiaoxiao Yu, Peng Zhao, You Zhou, Chun Huang, Li‐Sheng Wang, Yan‐Dong Wu, An‐Xin Wu
Abstract
A novel iodine promoted cyclization of enaminone with aryl methyl ketones has been developed as a straightforward method for constructing 2-hydroxy-pyrrol-3(2 H )-ones. This strategy affords structurally diverse 2-hydroxy-pyrrol-3(2 H )-ones rings in high yields. Moreover, a quarternary alcohol has been constructed efficiently in the reaction. Product purification required only washing with CH 2 Cl 2 solvent, thereby avoiding traditional chromatography and recrystallization, making this an example of group-assisted purification chemistry.
Topics & Concepts
ChemistryIodineCycloadditionAlcoholRecrystallization (geology)SolventQuaternary carbonOrganic chemistryArylColumn chromatographyCombinatorial chemistryCatalysisEnantioselective synthesisAlkylPaleontologyBiologySynthesis and Characterization of PyrrolesOxidative Organic Chemistry ReactionsSynthesis and Reactivity of Heterocycles