ArticleNature communications2021
Modular synthesis of chiral 1,2-dihydropyridines via Mannich/Wittig/cycloisomerization sequence that internally reuses waste.
Article in Nature communications, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 6 papers.
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Who cites it
6 citing papers in PubMed, 32 citations in OpenAlex.
- Rapid Access to 1,2,3,4-Tetrasubstituted Benzenes and 3‑Alkenyl-1,2-dihydropyridines.ACS omega · 2026Article
- Beyond Wittig Olefination: Phosphorus Ylide as a Ring-Expansion Reagent for Dibenzocycloheptanone Synthesis.JACS Au · 2025Article
- Gold-Catalyzed Amine Cascade Addition to Diyne-Ene: Enantioselective Synthesis of 1,2-Dihydropyridines.Angewandte Chemie (International ed. in English) · 2023Article
- Skeletal remodeling of chalcone-based pyridinium salts to access isoindoline polycycles and their bridged derivatives.Chemical science · 2021Article
- Mo-Catalyzed One-Pot Synthesis of N-Polyheterocycles from Nitroarenes and Glycols with Recycling of the Waste Reduction Byproduct. Substituent-Tuned Photophysical Properties.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Article
- Cascade aza-Wittig/6π-Electrocyclization in the Synthesis of 1,6-Dihydropyridines.Organic letters · 2021Article
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Authors and funding
5 authors at 3 institutions in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
1,2-Dihydropyridines are valuable and reactive synthons, and particularly useful precursors to synthesize piperidines and pyridines that are among the most common structural components of pharmaceuticals. However, the catalytic enantioselective synthesis of structurally diverse 1,2-dihydropyridines is limited to enantioselective addition of nucleophiles to activated pyridines. Here, we report a modular organocatalytic Mannich/Wittig/cycloisomerization sequence as a flexible strategy to access chiral 1,2-dihydropyridines from N-Boc aldimines, aldehydes, and phosphoranes, using a chiral amine catalyst. The key step in this protocol, cycloisomerization of chiral N-Boc δ-amino α,β-unsaturated ketones recycles the waste to improve the yield. Specifically, recycling by-product water from imine formation to gradually release the true catalyst HCl via hydrolysis of SiCl
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Registered trials
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