ArticleAngewandte Chemie (International ed. in English)2023
Enantioselective Hydroalkenylation and Hydroalkynylation of Alkenes Enabled by a Transient Directing Group: Catalyst Generality through Rigidification.
Article in Angewandte Chemie (International ed. in English), 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 7 papers.
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Who cites it
7 citing papers in PubMed.
- Catalytic Functionalization of Unactivated π-Bonds Enabled by Bidentate Directing Auxiliaries.Angewandte Chemie (International ed. in English) · 2026Review
- Recognition of a Conserved Minimal Catalaphile Explains Catalyst Generality in Enantioselective Nitroalkene Reductions.ACS catalysis · 2026Article
- Chemo-divergent and regioselective branched cross-hydroalkenylation of electron-deficient olefins and vinylarenes directed by (NHC)Ni(II) catalysts.Nature communications · 2026Article
- Noncovalent interaction-driven regio- and enantioselective hydroalkynylation of unactivated alkenes to access remote chiral nitriles.Science advances · 2025Article
- Cu(II)-Catalyzed Hydrofunctionalization of Unactivated Alkynes via π-Lewis Acid Activation.Journal of the American Chemical Society · 2025Article
- Remote-carbonyl-directed sequential Heck/isomerization/C(spNature communications · 2024Article
- Enhanced Excited-State Hydricity of Pd-H Allows for Unusual Head-to-Tail Hydroalkenylation of Alkenes.Journal of the American Chemical Society · 2023Article
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8 authors.
Funding
Abstract
The catalytic enantioselective synthesis of α-chiral alkenes and alkynes represents a powerful strategy for rapid generation of molecular complexity. Herein, we report a transient directing group (TDG) strategy to facilitate site-selective palladium-catalyzed reductive Heck-type hydroalkenylation and hydroalkynylation of alkenylaldehyes using alkenyl and alkynyl bromides, respectively, allowing for construction of a stereocenter at the δ-position with respect to the aldehyde. Computational studies reveal the dual beneficial roles of rigid TDGs, such as L-tert-leucine, in promoting TDG binding and inducing high levels of enantioselectivity in alkene insertion with a variety of migrating groups.
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