ArticleNature chemistry2024
Copper-catalysed asymmetric hydroboration of alkenes with 1,2-benzazaborines to access chiral naphthalene isosteres.
Article in Nature chemistry, 2024. 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.
- Substituent-rebound skeletal editing for precise boron-to-carbon single-atom swapping.Nature communications · 2026Article
- Copper-Catalyzed Asymmetric Hydroboration of Alkynes to C-N Axially Chiral Azaborines via Dynamic Kinetic Resolution.Angewandte Chemie (International ed. in English) · 2026Article
- A general photoinduced manganese-catalyzed platform for the sequential difunctionalization of [1.1.1]propellane.Science advances · 2026Article
- Catalytic asymmetric construction of remote P or other heteroatom (Si/S) stereogenic axially chiral scaffolds.Chemical science · 2026Article
- Organocatalysed three-component modular synthesis of BN isosteres and BN-2,1-azaboranaphthalenes via Wolff-type rearrangement.Nature chemistry · 2026Article
- Core diversification using 1,2-oxaborines as a versatile molecular platform.Nature chemistry · 2026Article
- Article
- Expedient access to bora-butenolide bioisosteres by counteranion-mediated trans-hydroboration of alkynes.Nature communications · 2025Article
- Synthesis of strained, air-stable boracycles via boron-carbon-centred diradicals.Nature chemistry · 2025Article
- Enantioselective construction of C-B axially chiral alkenylborons by nickel-catalyzed radical relayed reductive coupling.Nature communications · 2024Article
Corrections and comments
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Authors and funding
8 authors.
Funding
Abstract
Bioisosteric replacement has emerged as a clear strategy for drug-structure optimization. Naphthalene is the core element of many chiral pharmaceuticals and drug candidates. However, as a promising isostere of naphthalene, the chiral version of 1,2-benzazaborine has rarely been explored due to the lack of efficient synthetic methods. Here we describe a copper-catalysed enantioselective hydroboration of alkenes with 1,2-benzazaborines. The method provides a general platform for the atom-economic and efficient construction of diverse chiral 1,2-benzazaborine compounds (more than 60 examples) that bear a 2-carbon-stereogenic centre or allene skeleton in high yields and excellent enantioselectivities. Three 1,2-benzazaborine analogues of bioactive chiral naphthalene-containing molecules have been prepared, and a series of transformations around chiral 1,2-benzazaborines have also been developed. Notably, the hydroboration process of this study reveals that the identity of 1,2-benzazaborine plays an essential role in the rate-determining step and catalyst resting state.
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.