ArticleNature communications2024
Catalytic enantioselective intramolecular hydroamination of alkenes using chiral aprotic cyclic urea ligand on manganese (II).
Article in Nature communications, 2024. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 4 papers.
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Who cites it
4 citing papers in PubMed.
- Catalytic Enantioselective Intramolecular Aza-Michael Addition to α,β-Unsaturated Esters.Angewandte Chemie (International ed. in English) · 2026Article
- Computational and Experimental Studies on the α-Functionalization of Ketones Using Domino Reactions: A Strategy to Increase Chemoselectivity at the α-Carbon of Ketones.Molecules (Basel, Switzerland) · 2025Article
- Ni-Catalyzed Regioselective Alkylarylation of Unactivated Alkenes in Amines Enabled by Cooperative Ligand Effects of Nitriles and Electron-Deficient Alkenes.Journal of the American Chemical Society · 2025Article
- Anti-Neuroinflammatory Effects of Prenylated Indole Alkaloids from the Antarctic FungusMolecules (Basel, Switzerland) · 2025Article
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Authors and funding
7 authors.
Funding
Abstract
Asymmetric catalysis for enantioselective intramolecular hydroamination of alkenes is a critical method in the construction of enantioenriched nitrogen-containing rings, often prevalent in biologically active compounds and natural products. Herein, we demonstrate a facile enantioselective intramolecular hydroamination of alkenes for the synthesis of chiral pyrrolidine, piperidine, and indoline moieties, using a manganese (II) chiral aprotic cyclic urea catalyst. The cyclic ligand hinders the inversion of the N atom of the urea and effectively discriminate between the enantiomers of substrates. High-resolution mass spectrometry, deuterium labeling experiments, and molecular orbital energy analysis clearly reveal the intermediates and mechanism of the transformation. As a key step, oxygen coordination by chiral aprotic urea presents a robust control over the asymmetric intra-HA reaction through the involvement of a convergent assembly of two vital intermediates (Mn-N and C-Mn-Br), providing access to chiral cyclic amine systems in high yields with excellent enantioselectivity.
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Registered trials
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