ArticleNature communications2022
Enantioselective synthesis of α-aminoboronates by NiH-catalysed asymmetric hydroamidation of alkenyl boronates.
Article in Nature communications, 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 10 papers.
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Who cites it
10 citing papers in PubMed.
- Diastereodivergent Hydroamidation of Methylenecyclohexanes With Differentiated Active Catalytic Species.Angewandte Chemie (International ed. in English) · 2026Article
- Transition-Metal Hydride Catalysis Meets Nitrenoid Transfer: Design Principles for Precision C-N Bond Formation.Accounts of chemical research · 2026Article
- Enantioselective propargylic amination and related tandem sequences to α-tertiary ethynylamines and azacycles.Nature chemistry · 2024Article
- NiH-catalyzed C-N bond formation: insights and advancements in hydroamination of unsaturated hydrocarbons.Chemical science · 2024Review
- Ni-Catalyzed 1,1- and 1,3-Aminoboration of Unactivated Alkenes.Journal of the American Chemical Society · 2023Article
- Recent Progress in NiH-Catalyzed Linear or Branch Hydrofunctionalization of Terminal or Internal Alkenes.Topics in current chemistry (Cham) · 2023Review
- Copper-catalyzed [1,3]-nitrogen rearrangement ofChemical science · 2023Article
- Nickel-Catalyzed 1,1-Aminoborylation of Unactivated Terminal Alkenes.ACS catalysis · 2023Article
- Enantioselective Synthesis of α-Aminoboronic Acid Derivatives via Copper-Catalyzed N-Alkylation.Journal of the American Chemical Society · 2023Article
- Rhodium(III)-Catalyzed Anti-Markovnikov Hydroamidation of Unactivated Alkenes Using Dioxazolones as Amidating Reagents.Journal of the American Chemical Society · 2022Article
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Authors and funding
5 authors.
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Abstract
Chiral α-aminoboronic acids and their derivatives are generally useful as bioactive compounds and some have been approved as therapeutic agents. Here we report a NiH-catalysed asymmetric hydroamidation process that with a simple amino alcohol ligand can easily produce a wide range of highly enantioenriched α-aminoboronates from alkenyl boronates and dioxazolones under mild conditions. The reaction is proposed to proceed by an enantioselective hydrometallation followed by an inner-sphere nitrenoid transfer and C-N bond forming sequence. The synthetic utility of this transformation was demonstrated by the efficient synthesis of a current pharmaceutical agent, Vaborbactam.
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