ArticleChemical science2020
Introduction of a 7-aza-6-MeO-indoline auxiliary in Lewis-acid/photoredox cooperative catalysis: highly enantioselective aminomethylation of α,β-unsaturated amides.
Article in Chemical science, 2020. 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.
- Acyl-oxyallenes as α,β-unsaturated ketone surrogates for Giese radical addition.Chemical science · 2026Article
- Progress in Catalytic Asymmetric Reactions with 7-Azaindoline as the Directing Group.Molecules (Basel, Switzerland) · 2023Review
- Visible-light-induced chemo-, diastereo- and enantioselective α-C(spChemical science · 2023Article
- Enantioselective Giese Additions of Prochiral α-Amino Radicals.Journal of the American Chemical Society · 2022Article
- Regio-, Diastereo-, and Enantioselective Decarboxylative Hydroaminoalkylation of Dienol Ethers Enabled by Dual Palladium/Photoredox Catalysis.Angewandte Chemie (International ed. in English) · 2022Article
- Recent developments in enantioselective photocatalysis.Beilstein journal of organic chemistry · 2020Review
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Authors and funding
3 authors.
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Abstract
An efficient cooperative chiral Lewis acid/photoredox catalytic system for engaging highly reactive radicals in highly enantioselective conjugate addition to α,β-unsaturated carbonyls is highly desirable. Direct photoexcitation of unbound substrates typically induces undesired background pathways for racemic products and remains a formidable challenge to be addressed in the area of enantioselective photocatalysis. Herein, we report a cooperative catalytic system comprising a chiral Cu(i) complex and an Ir(iii) photocatalyst fueled by visible-light irradiation that allows for seamless integration of the catalytic formation of α-amino alkyl radicals and subsequent enantioselective addition to α,β-unsaturated amides. A 7-aza-6-MeO-indoline attachment on the amide substrates plays a pivotal role in suppressing the undesired pathways, resulting in excellent enantioselectivity and enabling expedited access to valuable γ-aminobutyramides. The indoline amide was readily diversified with full recovery of the azaindoline attachment, highlighting the synthetic utility of this cooperative catalytic system.
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