ArticleAngewandte Chemie (International ed. in English)2021
Photochemical Organocatalytic Regio- and Enantioselective Conjugate Addition of Allyl Groups to Enals.
Article in Angewandte Chemie (International ed. in English), 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 9 papers.
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Who cites it
9 citing papers in PubMed.
- The Diarylprolinol Silyl Ethers: After 20 Years Still Opening New Doors in Asymmetric Catalysis.Angewandte Chemie (International ed. in English) · 2026Review
- Selective Synthesis of α,α-Difluoro- and α-Monofluoro Methylene Substituted Arenes by Defluoro C-C Bond Coupling.Organic letters · 2025Article
- Catalytic prenyl conjugate additions for synthesis of enantiomerically enriched PPAPs.Science (New York, N.Y.) · 2024Article
- Consecutive π-Lewis acidic metal-catalysed cyclisation/photochemical radical addition promoted byChemical science · 2024Article
- Inexpensive and bench stable diarylmethylium tetrafluoroborates as organocatalysts in the light mediated hydrosulfonylation of unactivated alkenes.Chemical science · 2023Article
- Recent Advances in Asymmetric Synthesis of Pyrrolidine-Based Organocatalysts and Their Application: A 15-Year Update.Molecules (Basel, Switzerland) · 2023Review
- Arene Activation through Iminium Ions: Product Diversity from Intramolecular Photocycloaddition Reactions.Angewandte Chemie (International ed. in English) · 2022Article
- Synergistic Strategies in Aminocatalysis.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Review
- Photochemical Organocatalytic Regio- and Enantioselective Conjugate Addition of Allyl Groups to Enals.Angewandte Chemie (International ed. in English) · 2021Article
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3 authors.
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Abstract
We report the first catalytic enantioselective conjugate addition of allyl groups to α,β-unsaturated aldehydes. The chemistry exploits the visible-light-excitation of chiral iminium ions to activate allyl silanes towards the formation of allylic radicals, which are then intercepted stereoselectively. The underlying radical mechanism of this process overcomes the poor regio- and chemoselectivity that traditionally affects the conjugate allylation of enals proceeding via polar pathways. We also demonstrate how this organocatalytic strategy could selectively install a valuable prenyl fragment at the β-carbon of enals.
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