ArticleJournal of the American Chemical Society2021
Ligand Conformational Flexibility Enables Enantioselective Tertiary C-B Bond Formation in the Phosphonate-Directed Catalytic Asymmetric Alkene Hydroboration.
Article in Journal of the American Chemical Society, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 7 papers.
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7 citing papers in PubMed, 48 citations in OpenAlex.
- Theoretical study on ligand conformational self-adaptation for modulating reactivity.Scientific reports · 2024Article
- Impact of Model Selection and Conformational Effects on the Descriptors for In Silico Screening Campaigns: A Case Study of Rh-Catalyzed Acrylate Hydrogenation.The journal of physical chemistry. C, Nanomaterials and interfaces · 2024Article
- Nickel-Catalyzed Suzuki-Miyaura Coupling in Water for the Synthesis of 2-Aryl Allyl Phosphonates and Sulfones.The Journal of organic chemistry · 2024Article
- Ratcheting synthesis.Nature reviews. Chemistry · 2024Review
- How mono- and diphosphine ligands alter regioselectivity of the Rh-catalyzed annulative cleavage of bicyclo[1.1.0]butanes.Nature communications · 2022Article
- Article
- Hydrogen Atom Transfer Driven Enantioselective Minisci Reaction of Alcohols.Angewandte Chemie (International ed. in English) · 2022Article
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Authors and funding
5 authors at 3 institutions in 1 country.
Funding
Abstract
Conformationally flexible ancillary ligands have been widely used in transition metal catalysis. However, the benefits of using flexible ligands are often not well understood. We performed density functional theory (DFT) and experimental studies to elucidate the mechanisms and the roles of conformationally flexible α,α,α',α'-tetraaryldioxolane-4,5-dimethanol (TADDOL)-derived ligands on the reactivity and selectivity in the Rh-catalyzed asymmetric hydroboration (CAHB) of alkenes. DFT calculations and deuterium labeling studies both indicated that the most favorable reaction pathway involves an unusual tertiary C-B bond reductive elimination to give high levels of regio- and enantioselectivities. Here, the asymmetric construction of the fully substituted carbon center is promoted by the flexibility of the TADDOL backbone, which leads to two ligand conformations with distinct steric environments in different steps of the catalytic cycle. A pseudo-chair ligand conformation is preferred in the rate-determining tertiary benzylic C-B reductive elimination. The less hindered steric environment with this conformation allows the benzylic group to bind to the Rh center in an η
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