ArticleJournal of the American Chemical Society2020
Diastereo- and Enantioselective Synthesis of Homoallylic Amines Bearing Quaternary Carbon Centers.
Article in Journal of the American Chemical Society, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 14 papers.
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Who cites it
14 citing papers in PubMed.
- Enantio- and Site-Selective Synthesis of α-Substituted Hydrazines, Pyrazolidines, and Tertiary Alcohols by Copper-Catalyzed Allylic C-N and C-O Bond Formation.Journal of the American Chemical Society · 2026Article
- Direct Activation of Sulfides by C-H Oxidation with Photoexcited Nitroarenes: Formal Manipulations of the C─S Bond.Angewandte Chemie (International ed. in English) · 2025Article
- Merging Ketyl Radical Chemistry and Allylboration via Strain Release: One-Pot Multicomponent Access to Sterically Congested Ketone-Functionalized Organoborons.Organic letters · 2025Article
- Palladium-catalyzed cross-coupling ofRSC advances · 2025Article
- Strain-release enables access to carbonyl conjugated allylic diborons and alkenyl boronates having multiple contiguous stereocenters in a one-pot process.Chemical science · 2025Article
- Axially chiral α-boryl-homoallenyl boronic esters as versatile toolbox for accessing centrally and axially chiral molecules.Nature communications · 2024Article
- The current utility and future potential of multiborylated alkanes.Nature reviews. Chemistry · 2024Review
- A Catalytic Method for the Enantioselective Synthesis of α-Quaternary Ketones, α-Ketoesters and Aldehydes.Angewandte Chemie (International ed. in English) · 2023Article
- Article
- Access to Chiral Diamine Derivatives through Stereoselective Cu-Catalyzed Reductive Coupling of Imines and Allenamides.The Journal of organic chemistry · 2021Article
- Diastereo-, Enantio-, andOrganic letters · 2020Article
- Sulfonate N-Heterocyclic Carbene-Copper Complexes: Uniquely Effective Catalysts for Enantioselective Synthesis of C-C, C-B, C-H, and C-Si Bonds.Angewandte Chemie (International ed. in English) · 2020Review
- Synthesis of Quaternary Carbon Stereogenic Centers by Diastereoselective Conjugate Addition of Boron-Stabilized Allylic Nucleophiles to Enones.Journal of the American Chemical Society · 2020Article
- Cu-Catalyzed Diastereo- and Enantioselective Reactions of γ,γ-Disubstituted Allyldiboron Compounds with Ketones.Angewandte Chemie (International ed. in English) · 2020Article
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3 authors.
Funding
Abstract
A Cu-catalyzed method for the efficient enantio- and diastereoselective synthesis of chiral homoallylic amines bearing a quaternary carbon and an alkenylboron is disclosed. Transformations are promoted by a readily prepared (phosphoramidite)-Cu complex and involve bench-stable γ,γ-disubstituted allyldiborons and benzyl imines; products are obtained in up to 82% yield, >20:1 dr, and >99:1 er. Reactions proceed via stereodefined boron-stabilized allylic Cu species formed by an enantioselective transmetalation. Utility of the 1-amino-3-alkenylboronate products is highlighted by a variety of synthetic transformations.
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