ArticleAngewandte Chemie (International ed. in English)2019
Ligand-Controlled Regiodivergent Enantioselective Rhodium-Catalyzed Alkene Hydroboration.
Article in Angewandte Chemie (International ed. in English), 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 6 papers.
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Who cites it
6 citing papers in PubMed.
- Copper-Catalyzed Asymmetric Hydroboration of Alkynes to C-N Axially Chiral Azaborines via Dynamic Kinetic Resolution.Angewandte Chemie (International ed. in English) · 2026Article
- Theoretical study on ligand conformational self-adaptation for modulating reactivity.Scientific reports · 2024Article
- Cobalt-Catalyzed Enantioselective Hydroboration of α-Substituted Acrylates.Journal of the American Chemical Society · 2024Article
- Asymmetric Catalytic Hydroboration of Enol Carbamates Enables an Enantioselective Matteson Homologation.Synlett : accounts and rapid communications in synthetic organic chemistry · 2023Article
- Catalyst-controlled selective borocarbonylation of benzylidenecyclopropanes: regiodivergent synthesis of γ-vinylboryl ketones and β-cyclopropylboryl ketones.Chemical science · 2022Article
- 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
Corrections and comments
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Authors and funding
3 authors.
Funding
Abstract
Regiocontrol in the rhodium-catalyzed boration of vinyl arenes is typically dominated by the presence of the conjugated aryl substituent. However, small differences in TADDOL-derived chiral monophosphite ligands can override this effect and direct rhodium-catalyzed hydroboration of β-aryl and β-heteroaryl methylidenes by pinacolborane to selectively produce either chiral primary or tertiary borated products. The regiodivergent behavior is coupled with enantiodivergent addition of the borane. The nature of the TADDOL backbone substituents and that of the phosphite moiety function synergistically to direct the sense and extent of regioselectivity and enantioinduction. Twenty substrates are shown to undergo each reaction mode with regioselectivity values reaching greater than 20:1 and enantiomer ratios reaching up to 98:2. A variety of subsequent transformations illustrate the potential utility of each product.
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