ArticleNature chemistry2017
Direct, enantioselective α-alkylation of aldehydes using simple olefins.
Article in Nature chemistry, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 39 papers.
What it found
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Who cites it
39 citing papers in PubMed, 209 citations in OpenAlex.
- Synthesis and Organocatalytic Activity of Imidazolidinone Organocatalysts.Molecules (Basel, Switzerland) · 2026Article
- The Diarylprolinol Silyl Ethers: After 20 Years Still Opening New Doors in Asymmetric Catalysis.Angewandte Chemie (International ed. in English) · 2026Review
- Iridium-Catalyzed Stereoselective α-Alkylation of α-Hydroxy Ketones with Minimally Polarized Alkenes.Journal of the American Chemical Society · 2026Article
- Dual-Mode Thio-MacMillan Organocatalysts: Stereoselective Diels-Alder Reactions or Sacrificial Self-Cyclization to N-Bridged Bicyclic Lactams.Chemistry (Weinheim an der Bergstrasse, Germany) · 2026Article
- Recent Advances in the Utilization of Chiral Covalent Organic Frameworks for Asymmetric Photocatalysis.Molecules (Basel, Switzerland) · 2024Review
- Construction of axially chiral molecules enabled by photoinduced enantioselective reactions.Chemical science · 2024Review
- A directed enolization strategy enables by-product-free construction of contiguous stereocentres en route to complex amino acids.Nature chemistry · 2024Article
- 1,5-Hydrogen atom transfer of α-iminyl radical cations: a new platform for relay annulation for pyridine derivatives and axially chiral heterobiaryls.Chemical science · 2024Article
- Asymmetric C-H Dehydrogenative Alkenylation via a Photo-induced Chiral α‑Imino Radical Intermediate.Nature communications · 2024Article
- Article
- Asymmetric Photoaerobic Lactonization and Aza-Wacker Cyclization of Alkenes Enabled by Ternary Selenium-Sulfur Multicatalysis.ACS catalysis · 2023Article
- Photocatalyzed Direct α-Alkylation of Esters Using Styrenes.Advanced synthesis & catalysis · 2023Article
- Catalytic asymmetric defluorinative allylation of silyl enol ethers.Chemical science · 2023Article
- Article
- An enantioselective four-component reaction via assembling two reaction intermediates.Nature communications · 2022Article
- Catalytic transfer hydrogenation of NScience advances · 2022Article
- Synergistic Strategies in Aminocatalysis.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Review
- Diverse synthesis of C2-linked functionalized molecules via molecular glue strategy with acetylene.Nature communications · 2022Article
- Bond Energies of Enamines.ACS omega · 2022Article
- Photoredox-Catalyzed C-H Functionalization Reactions.Chemical reviews · 2022Review
Corrections and comments
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Authors and funding
5 authors at 1 institution in 1 country.
Funding
Abstract
Although the α-alkylation of ketones has already been established, the analogous reaction using aldehyde substrates has proven surprisingly elusive. Despite the structural similarities between the two classes of compounds, the sensitivity and unique reactivity of the aldehyde functionality has typically required activated substrates or specialized additives. Here, we show that the synergistic merger of three catalytic processes-photoredox, enamine and hydrogen-atom transfer (HAT) catalysis-enables an enantioselective α-aldehyde alkylation reaction that employs simple olefins as coupling partners. Chiral imidazolidinones or prolinols, in combination with a thiophenol, iridium photoredox catalyst and visible light, have been successfully used in a triple catalytic process that is temporally sequenced to deliver a new hydrogen and electron-borrowing mechanism. This multicatalytic process enables both intra- and intermolecular aldehyde α-methylene coupling with olefins to construct both cyclic and acyclic products, respectively. With respect to atom and step-economy ideals, this stereoselective process allows the production of high-value molecules from feedstock chemicals in one step while consuming only photons.
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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.