ArticleThe Journal of organic chemistry2022
Photocatalytic Reductive Olefin Hydrodifluoroalkylation Enabled by Tertiary Amine Reductants Compatible with Complex Systems.
Article in The Journal of organic chemistry, 2022. 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.
- A unified platform for the rapid assembly of glutarimides for Cereblon E3 ligase modulatory drugs.Nature communications · 2026Article
- Single-carbon-atom transfer toChemical science · 2025Article
- Catalyst-Controlled Site-Selective and Epimer-Selective Hydrogenations of Thiostrepton.Journal of the American Chemical Society · 2025Article
- Enantioselective Hydrodifluoroalkylation of Alkenes with Conformationally Tuned Peptidyl Hydrogen Atom Transfer Catalysts.Journal of the American Chemical Society · 2025Article
- Photocatalytic Synthesis of Difluorinated Glycoamino Acids and Neoglycopeptides via Hydrodifluoroacetamidation of Vinyl-C-glycosides.The Journal of organic chemistry · 2025Article
- Simplified Modular Access to Enantiopure 1,2-Aminoalcohols via Ni-Electrocatalytic Decarboxylative Arylation.Journal of the American Chemical Society · 2024Article
Corrections and comments
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Authors and funding
2 authors.
Funding
Abstract
Noncanonical amino acids (NCAAs) are imperative to many facets of chemistry and biology. Herein, we report a method for the reductive hydrodifluoroalkylation of olefins that utilizes triethylamine base as the terminal reductant. The alkene acceptors include a range of electronically diverse alkenes, chief among them, dehydroalanine in variously protected forms, which provides access to synthetically relevant NCAA scaffolds under mild and general reaction conditions. We have demonstrated that a chiral auxiliary may be incorporated to provide diastereocontrol for pro-stereogenic substrates. Mechanistically motivated experiments provide some insight into the reaction mechanism, which supports a terminal step involving proton transfer for electron-poor olefins, while H atom transfer assisted by a thiol cocatalyst may complete the catalytic cycle for electron-rich olefins. The protocol is found to be compatible with additions to complex molecules, including the natural product thiostrepton.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the Socratic graph.