ArticleAngewandte Chemie (International ed. in English)2022
Enantioselective Synthesis of Tertiary β-Boryl Amides by Conjunctive Cross-Coupling of Alkenyl Boronates and Carbamoyl Chlorides.
Article in Angewandte Chemie (International ed. in English), 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 10 papers.
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10 citing papers in PubMed.
- Nickel-Catalyzed Boron-Mediated Saturative Trifunctionalization of Alkynes.Angewandte Chemie (International ed. in English) · 2026Article
- Pd-Catalyzed Arylative Lossen Rearrangement: Synthesis of Secondary Amines from Aryl/Alkyl Carboxylic Acids and Aryl Halides.Journal of the American Chemical Society · 2026Article
- Catalytic Stereospecific Construction of Aminocyclopropanes from β-Boryl Amides.Journal of the American Chemical Society · 2026Article
- Strain-Release Induced 1,2-Metallate Rearrangement of Geminal Diborons: Multicomponent 1,5-Difunctionalization via Ring-Opening Coupling.Angewandte Chemie (International ed. in English) · 2026Article
- Ni-Catalyzed Regioselective Alkylarylation of Unactivated Alkenes in Amines Enabled by Cooperative Ligand Effects of Nitriles and Electron-Deficient Alkenes.Journal of the American Chemical Society · 2025Article
- Merging Organocatalysis with 1,2-Boronate Rearrangement: A Lewis Base-Catalyzed Asymmetric Multicomponent Reaction.Journal of the American Chemical Society · 2024Article
- Chemical Upcycling of PET into a Morpholine Amide as a Versatile Synthetic Building Block.ACS organic & inorganic Au · 2023Article
- Enantioselective Construction of Carbocyclic and Heterocyclic Tertiary Boronic Esters by Conjunctive Cross-Coupling Reaction.Journal of the American Chemical Society · 2023Article
- Iridium-Catalyzed Asymmetric Difunctionalization of C-C σ-Bonds Enabled by Ring-Strained Boronate Complexes.Journal of the American Chemical Society · 2023Article
- Annulative coupling of vinylboronic esters: aryne-triggered 1,2-metallate rearrangement.Chemical science · 2022Article
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4 authors.
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Abstract
Synthesis of versatile β tert-boryl amides is accomplished by conjunctive cross-coupling of α-substituted alkenyl boron "ate" complexes and carbamoyl chloride electrophiles. This reaction can be accomplished in an enantioselective fashion using a palladium catalyst in combination with MandyPhos. The addition of water results in enhanced chemoselectivity for the conjunctive coupling product relative to the Suzuki-Miyaura cross-coupling product. Transformations of the reaction products were examined as well as application to the synthesis of (+)-adalinine.
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