ArticleAngewandte Chemie (International ed. in English)2016
Synthesis of Chiral Tertiary Boronic Esters by Oxime-Directed Catalytic Asymmetric Hydroboration.
Article in Angewandte Chemie (International ed. in English), 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 18 papers.
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Who cites it
18 citing papers in PubMed.
- Enantioselective synthesis of tertiary boronic esters through catalytic asymmetric reversed hydroboration.Nature communications · 2021Article
- Ligand Conformational Flexibility Enables Enantioselective Tertiary C-B Bond Formation in the Phosphonate-Directed Catalytic Asymmetric Alkene Hydroboration.Journal of the American Chemical Society · 2021Article
- Rhodium-catalysed selective C-C bond activation and borylation of cyclopropanes.Chemical science · 2021Article
- 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
- Nickel-Catalyzed Arylboration of Alkenylarenes: Synthesis of Boron-Substituted Quaternary Carbons and Regiodivergent Reactions.Angewandte Chemie (International ed. in English) · 2019Article
- Ligand-Controlled Regiodivergent Enantioselective Rhodium-Catalyzed Alkene Hydroboration.Angewandte Chemie (International ed. in English) · 2019Article
- Facile access to functionalized chiral secondary benzylic boronic estersChemical science · 2019Article
- Cationic Co(I)-Intermediates for Hydrofunctionalization Reactions: Regio- and Enantioselective Cobalt-Catalyzed 1,2-Hydroboration of 1,3-Dienes.Journal of the American Chemical Society · 2019Article
- Phosphonate-Directed Catalytic Asymmetric Hydroboration: Delivery of Boron to the More Substituted Carbon, Leading to Chiral Tertiary Benzylic Boronic Esters.ACS catalysis · 2018Article
- Enantioselective Construction of Tertiary Boronic Esters by Conjunctive Cross-Coupling.Angewandte Chemie (International ed. in English) · 2018Article
- Nickel(0)-catalyzed linear-selective hydroarylation of unactivated alkenes and styrenes with aryl boronic acids.Chemical science · 2018Article
- Rhodium-catalyzed asymmetric hydroboration of γ,δ-unsaturated amide derivatives: δ-borylated amides.Chemical communications (Cambridge, England) · 2018Article
- Mechanistic Studies of Copper-Catalyzed Asymmetric Hydroboration of Alkenes.Journal of the American Chemical Society · 2017Article
- Enantioselective Rhodium(III)-Catalyzed Markovnikov Hydroboration of Unactivated Terminal Alkenes.Journal of the American Chemical Society · 2017Article
- Enantioselective palladium-catalyzed diboration of 1,1-disubstituted allenes.Chemical science · 2017Article
- Enantioselective γ-borylation of unsaturated amides and stereoretentive Suzuki-Miyaura cross-coupling.Chemical science · 2017Article
- Synthesis of Chiral Tertiary Boronic Esters: Phosphonate-Directed Catalytic Asymmetric Hydroboration of Trisubstituted Alkenes.Journal of the American Chemical Society · 2017Article
- Remarkably Facile Borane-Promoted, Rhodium-Catalyzed Asymmetric Hydrogenation of Tri- and Tetrasubstituted Alkenes.Journal of the American Chemical Society · 2017Article
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Authors and funding
4 authors.
Funding
Abstract
Chiral boronic esters are useful intermediates in asymmetric synthesis. We have previously shown that carbonyl-directed catalytic asymmetric hydroboration (CAHB) is an efficient approach to the synthesis of functionalized primary and secondary chiral boronic esters. We now report that the oxime-directed CAHB of alkyl-substituted methylidene and trisubstituted alkene substrates by pinacolborane (pinBH) affords oxime-containing chiral tertiary boronic esters with yields up to 87% and enantiomeric ratios up to 96:4 e.r. The utility of the method is demonstrated by the formation of chiral diols and O-substituted hydroxylamines, the generation of quaternary carbon stereocenters through carbon-carbon coupling reactions, and the preparation of chiral 3,4,4-trisubstituted isoxazolines.
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