ArticleNature communications2023
Catalytic enantioselective reductive alkynylation of amides enables one-pot syntheses of pyrrolidine, piperidine and indolizidine alkaloids.
Article in Nature communications, 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. An erratum has been issued. Cited by 5 papers.
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Who cites it
5 citing papers in PubMed, 40 citations in OpenAlex.
- Recent Advances in Intramolecular C─N Bond Formation for Pyrrolidine Synthesis.ChemistryOpen · 2026Review
- Total Synthesis of Isodaphlongamine H by Iridium-Catalyzed Reductive [3 + 2] Cycloaddition of N-Hydroxylactam.Angewandte Chemie (International ed. in English) · 2025Article
- α,β-Unsaturated Diazoketones as Building Blocks to Piperidine Alkaloids: Total Synthesis of (-)-Cassine.The Journal of organic chemistry · 2025Article
- Divergent alkynylative difunctionalization of amide bonds through C-O deoxygenation versus C-N deamination.Nature communications · 2025Article
- Further elaboration of the stereodivergent approach to chaetominine-type alkaloids: synthesis of the reported structures of aspera chaetominines A and B and revised structure of aspera chaetominine B.Beilstein journal of organic chemistry · 2025Article
Corrections and comments
- Erratum issued
Authors and funding
4 authors at 1 institution in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
The primary objective in synthetic organic chemistry is to develop highly efficient, selective, and versatile synthetic methodologies, which are essential for discovering new drug candidates and agrochemicals. In this study, we present a unified strategy for a one-pot, catalytic enantioselective synthesis of α-alkyl and α,α'-dialkyl pyrrolidine, piperidine, and indolizidine alkaloids using readily available amides and alkynes. This synthesis is enabled by the identification and development of an Ir/Cu/N-PINAP catalyzed highly enantioselective and chemoselective reductive alkynylation of α-unbranched aliphatic amides, which serves as the key reaction. This reaction is combined with Pd-catalyzed tandem reactions in a one-pot approach, enabling the collective, catalytic enantioselective total syntheses of eight alkaloids and an anticancer antipode with 90-98% ee. The methodology's enantio-divergence is exemplified by the one-step access to either enantiomer of alkaloid bgugaine.
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Registered trials
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