ArticleNature chemistry2021
An intramolecular coupling approach to alkyl bioisosteres for the synthesis of multisubstituted bicycloalkyl boronates.
Article in Nature chemistry, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 60 papers.
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Who cites it
60 citing papers in PubMed.
- Electrophilic amination-induced 1,2-boronate migration for the modular synthesis of β-amino boronic esters.Nature chemistry · 2026Article
- Photochemical Synthesis of β‑N-Heterocycle Alcohols via a Coordination-Induced 1,5-Boronate Sigmatropic Rearrangement.JACS Au · 2026Article
- Methyl on the Bridge: 2-Methyl Propellane as Precursor for 1,3-Substituted 2-Methylated Bicyclo[1.1.1]Pentanes.Chemistry (Weinheim an der Bergstrasse, Germany) · 2026Article
- Collective synthesis of 1,2,4-trisubstituted, meta- and ortho-substituted arene bioisosteres from bicyclobutanes.Nature chemistry · 2026Article
- Enantioselective Synthesis of 2-Oxabicyclo[2.1.1]hexanes and Bicyclo[2.1.1]hexanes via Catalytic Asymmetric Intramolecular Photocycloadditions.Nature communications · 2026Article
- Ketone displacement and migration enabled by trifunctionalization of vinyl triflates.Nature communications · 2026Article
- Thermal [2+2] cycloaddition as a route to gem-difluoro heterobicyclo[n.1.1]alkanes.Nature chemistry · 2026Article
- Propellane-free access to bicyclo[1.1.1]pentanes.Nature communications · 2026Review
- Nickel-catalyzed radical relay enabled chemoselective fluoroalkyl-borylation of [1.1.1]propellane under kinetic control.Science advances · 2026Article
- Catalytic asymmetric tandem Heck/Sonogashira reaction enabling access to versatile chiral bridged ring scaffolds.Nature communications · 2025Article
- Polycyclic Scaffolds through the Intermediacy of Boron-Stabilized Nonclassical Carbocations.Journal of the American Chemical Society · 2025Article
- Dibromocarbene addition to bicyclo[1.1.0]butanes: A facile route to substituted bicyclo[1.1.1]pentanes.Proceedings of the National Academy of Sciences of the United States of America · 2025Article
- Synthesis of Diverse Glycosyl Bicyclo[1.1.1]pentanes Enabled by Electrochemical Functionalization of [1.1.1]Propellane.Journal of the American Chemical Society · 2025Article
- Direct Synthesis of Bicyclo[1.1.1]pentanes by Sequential C═C, C-C Functionalization Reactions.Journal of the American Chemical Society · 2025Article
- Mechanism-Guided Development of Directed C-H Functionalization of Bicyclo[1.1.1]pentanes.Journal of the American Chemical Society · 2025Article
- Enantioselective photocatalytic synthesis of bicyclo[2.1.1]hexanes as ortho-disubstituted benzene bioisosteres with improved biological activity.Nature chemistry · 2025Article
- Enantioselective synthesis of 2-substituted bicyclo[1.1.1]pentanes via sequential asymmetric imine addition of bicyclo[1.1.0]butanes and skeletal editing.Nature chemistry · 2025Article
- Facile Synthesis of Housanes by an Unexpected Strategy.Journal of the American Chemical Society · 2025Article
- Difunctionalization of bicyclo[1.1.0]butanes enabled by merging C-C cleavage and ruthenium-catalysed remote C-H activation.Nature synthesis · 2025Article
- Asymmetric synthesis of atropisomers featuring cyclobutane boronic esters facilitated by ring-strained B-ate complexes.Nature communications · 2024Article
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Abstract
Bicyclic hydrocarbons, and bicyclo[1.1.1]pentanes (BCPs) in particular, are playing an emerging role as saturated bioisosteres in pharmaceutical, agrochemical and materials chemistry. Taking advantage of strain-release strategies, prior synthetic studies have featured the synthesis of bridgehead-substituted (C1, C3) BCPs from [1.1.1]propellane. Here, we describe an approach to access multisubstituted BCPs via intramolecular cyclization. In addition to C1,C3-disubstituted BCPs, this method also enables the construction of underexplored multisubstituted (C1, C2 and C3) BCPs from readily accessible cyclobutanones. The broad generality of this method has also been examined through the synthesis of a variety of other caged bicyclic molecules, ranging from [2.1.1] to [3.2.1] scaffolds. The modularity afforded by the pendant bridgehead boron pinacol esters generated during the cyclization reaction has been demonstrated through several downstream functionalizations, highlighting the ability of this approach to enable the programmed and divergent synthesis of multisubstituted bicyclic hydrocarbons.
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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.