ArticleNature2017
Catalytic allylic oxidation of internal alkenes to a multifunctional chiral building block.
Article in Nature, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 36 papers.
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Who cites it
36 citing papers in PubMed, 125 citations in OpenAlex.
- Atomically Dispersed Iron-Catalyzed Aerobic Hydroxylation of Allylic and Propargylic C─H Bonds.Angewandte Chemie (International ed. in English) · 2026Article
- [2+2] Photocycloaddition reactions of sulfinylamines with alkenes to access β-sultam derivatives.Nature chemistry · 2026Article
- Organocatalytic enantioselective synthesis of S(IV)-stereogenic sulfinamides enabled by an air-stable chiral phosphine.Nature chemistry · 2026Article
- Chemoenzymatic synthesis of pentalenolactones via stereoselective Riley oxidation by engineered P450Nature communications · 2026Article
- Copper-Catalyzed Asymmetric Cyclizative Sulfinamidation: Forging Indole-Based Stereogenic Sulfur(IV) Centers and Atropisomeric Chirality.ACS central science · 2025Article
- Allylic Amination of Alkenyl Alcohols: Simultaneous Control of Chemoselectivity and Enantioselectivity in Nitrene Transfer Using Ion-Paired Catalysts.ACS catalysis · 2025Article
- A general leaving group assisted strategy for synthesis of pentafluorosulfanyl allylic compounds.Science advances · 2025Article
- Photoinduced Copper-Catalyzed Enantioselective Allylic C(Journal of the American Chemical Society · 2025Article
- Asymmetric reductive arylation and alkenylation to access S-chirogenic sulfinamides.Nature communications · 2025Article
- Photoredox-catalyzed deoxygenative radical transformation of alcohols to sulfinamides.RSC advances · 2025Article
- Photoinduced Pd-Catalyzed Direct Sulfonylation of Allylic C-H Bonds.Angewandte Chemie (International ed. in English) · 2025Article
- Halide Perovskite Induces Halogen/Hydrogen Atom Transfer (XAT/HAT) for Allylic C-H Amination.Angewandte Chemie (International ed. in English) · 2025Article
- Bridging the information gap in organic chemical reactions.Nature chemistry · 2024Review
- Cooperative Cu/azodiformate system-catalyzed allylic C-H amination of unactivated internal alkenes directed by aminoquinoline.Nature communications · 2024Article
- Kinetically-driven reactivity of sulfinylamines enables direct conversion of carboxylic acids to sulfinamides.Chemical science · 2023Article
- Photocatalytic Carboxylate to Sulfinamide Switching Delivers a Divergent Synthesis of Sulfonamides and Sulfonimidamides.Journal of the American Chemical Society · 2023Article
- Copper-Catalyzed Regiodivergent Internal Allylic Alkylations.Angewandte Chemie (International ed. in English) · 2023Article
- Transfer freier Aminogruppen via α-Aminierung von Carbonylen.Angewandte Chemie (Weinheim an der Bergstrasse, Germany) · 2023Article
- Free Amino Group Transfer via α-Amination of Native Carbonyls.Angewandte Chemie (International ed. in English) · 2023Article
- Metalloradical approach for concurrent control in intermolecular radical allylic C-H amination.Nature chemistry · 2023Article
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Authors and funding
3 authors at 1 institution in 1 country.
Funding
Abstract
The stereoselective oxidation of hydrocarbons is one of the most notable advances in synthetic chemistry over the past fifty years. Inspired by nature, enantioselective dihydroxylations, epoxidations and other oxidations of unsaturated hydrocarbons have been developed. More recently, the catalytic enantioselective allylic carbon-hydrogen oxidation of alkenes has streamlined the production of pharmaceuticals, natural products, fine chemicals and other functional materials. Allylic functionalization provides a direct path to chiral building blocks with a newly formed stereocentre from petrochemical feedstocks while preserving the olefin functionality as a handle for further chemical elaboration. Various metal-based catalysts have been discovered for the enantioselective allylic carbon-hydrogen oxidation of simple alkenes with cyclic or terminal double bonds. However, a general and selective allylic oxidation using the more common internal alkenes remains elusive. Here we report the enantioselective, regioselective and E/Z-selective allylic oxidation of unactivated internal alkenes via a catalytic hetero-ene reaction with a chalcogen-based oxidant. Our method enables non-symmetric internal alkenes to be selectively converted into allylic functionalized products with high stereoselectivity and regioselectivity. Stereospecific transformations of the resulting multifunctional chiral building blocks highlight the potential for rapidly converting internal alkenes into a broad range of enantioenriched structures that can be used in the synthesis of complex target molecules.
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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 OpenQuestion graph.