ArticleChemical science2019
Facile access to functionalized chiral secondary benzylic boronic esters
Article in Chemical science, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 5 papers.
What it found
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The trial behind it
Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.
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Who cites it
5 citing papers in PubMed, 25 citations in OpenAlex.
- The current utility and future potential of multiborylated alkanes.Nature reviews. Chemistry · 2024Review
- Synthesis of substituted benzylboronates by light promoted homologation of boronic acids withChemical science · 2023Article
- Copper-Catalyzed Regio- and Enantioselective Hydroboration of Difluoroalkyl-Substituted Internal Alkenes.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2023Article
- 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
- Ligand-Controlled Regiodivergent Enantioselective Rhodium-Catalyzed Alkene Hydroboration.Angewandte Chemie (International ed. in English) · 2019Article
Corrections and comments
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Authors and funding
5 authors at 2 institutions in 1 country.
Funding
Abstract
Allylic and homoallylic phosphonates bearing an aryl or heteroaryl substituent at the γ- or δ-position undergo rhodium-catalyzed asymmetric hydroboration by pinacolborane to give functionalized chiral secondary benzylic boronic esters in yields up to 86% and enantiomer ratios up to 99 : 1. Compared to minimally-functionalized terminal and 1,1-disubstituted vinyl arenes, there are relatively few reports of efficient catalytic asymmetric hydroboration (CAHB) of more highly functionalized internal alkenes. Phosphonate substrates bearing a variety of common heterocyclic ring systems, including furan, indole, pyrrole and thiophene derivatives, as well as those bearing basic nitrogen substituents (
Identifiers
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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.