ArticleChemical science2017
Enantioselective γ-borylation of unsaturated amides and stereoretentive Suzuki-Miyaura cross-coupling.
Article in Chemical science, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 16 papers.
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Who cites it
16 citing papers in PubMed, 47 citations in OpenAlex.
- Rapid, Homogenous, B-Alkyl Suzuki-Miyaura Cross-Coupling of Boronic Esters.The Journal of organic chemistry · 2024Article
- Preparation of Chitosan-Composite-Film-Supported Copper Nanoparticles and Their Application in 1,6-Hydroboration Reactions ofMolecules (Basel, Switzerland) · 2022Article
- The Stereochemical Course of Pd-Catalyzed Suzuki Reactions Using Primary Alkyltrifluoroborate Nucleophiles.ACS catalysis · 2021Article
- Rhodium-catalysed selective C-C bond activation and borylation of cyclopropanes.Chemical science · 2021Article
- Stereoselectivity in Pd-catalysed cross-coupling reactions of enantioenriched nucleophiles.Nature reviews. Chemistry · 2020Article
- A General Approach to Stereospecific Cross-Coupling Reactions of Nitrogen-Containing Stereocenters.Chem · 2020Article
- Accessing 1,2-Substituted Cyclobutanes through 1,2-Azaborine Photoisomerization.Angewandte Chemie (International ed. in English) · 2019Article
- Palladium(0)-Catalyzed Directed syn-1,2-Carboboration and -Silylation: Alkene Scope, Applications in Dearomatization, and Stereocontrol by a Chiral Auxiliary.Angewandte Chemie (International ed. in English) · 2019Article
- Facile access to functionalized chiral secondary benzylic boronic estersChemical science · 2019Article
- Axial shielding of Pd(II) complexes enables perfect stereoretention in Suzuki-Miyaura cross-coupling of CspNature communications · 2019Article
- Enantiospecific Synthesis of ortho-Substituted 1,1-Diarylalkanes by a 1,2-Metalate Rearrangement/anti-SAngewandte Chemie (International ed. in English) · 2019Article
- Enantiodivergent Pd-catalyzed C-C bond formation enabled through ligand parameterization.Science (New York, N.Y.) · 2018Article
- Phosphonate-Directed Catalytic Asymmetric Hydroboration: Delivery of Boron to the More Substituted Carbon, Leading to Chiral Tertiary Benzylic Boronic Esters.ACS catalysis · 2018Article
- Chiral Aniline Synthesis via Stereospecific C(spOrganic letters · 2018Article
- Rhodium-catalyzed asymmetric hydroboration of γ,δ-unsaturated amide derivatives: δ-borylated amides.Chemical communications (Cambridge, England) · 2018Article
- Toward Generalization of Iterative Small Molecule Synthesis.Nature reviews. Chemistry · 2018Article
Corrections and comments
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Authors and funding
2 authors at 1 institution in 1 country.
Funding
Abstract
The rhodium-catalyzed, directed catalytic asymmetric hydroboration of γ,δ-unsaturated amides affords a direct route to chiral acyclic secondary γ-borylated carbonyl derivatives in high enantiomeric purity. In contrast to a similar β-borylated amide derivative, the γ-borylated amide undergoes Suzuki-Miyaura cross-coupling with stereoretention. The utility of the boronic ester products is further illustrated by other stereospecific C-B bond transformations leading to γ-amino acid derivatives, 1,4-amino alcohols, and 5-substituted-γ-lactone and γ-lactam ring systems.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.