ArticleNature communications2021
Direct catalytic asymmetric synthesis of α-chiral bicyclo[1.1.1]pentanes.
Article in Nature communications, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 23 papers.
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Who cites it
23 citing papers in PubMed, 71 citations in OpenAlex.
- The Diarylprolinol Silyl Ethers: After 20 Years Still Opening New Doors in Asymmetric Catalysis.Angewandte Chemie (International ed. in English) · 2026Review
- Nickel-catalyzed radical relay enabled chemoselective fluoroalkyl-borylation of [1.1.1]propellane under kinetic control.Science advances · 2026Article
- Direct Synthesis of Bicyclo[1.1.1]pentanes by Sequential C═C, C-C Functionalization Reactions.Journal of the American Chemical Society · 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
- Recent Advances in Radical Coupling Reactions Directly Involving Bicyclo[1.1.1]pentane (BCP).Topics in current chemistry (Cham) · 2025Review
- Beyond Strain Release: Delocalization-Enabled Organic Reactivity.The Journal of organic chemistry · 2024Article
- α-Amino bicycloalkylation through organophotoredox catalysis.Chemical science · 2024Article
- Radical-Mediated α-JACS Au · 2024Article
- Titanium catalyzed [2σ + 2π] cycloaddition of bicyclo[1.1.0]-butanes with 1,3-dienes for efficient synthesis of stilbene bioisosteres.Nature communications · 2024Article
- Enantioselective Synthesis of α-Chiral Bicyclo[1.1.1]pentanes via Multicomponent Asymmetric Allylic Alkylation.Organic letters · 2024Article
- Programmable late-stage functionalization of bridge-substituted bicyclo[1.1.1]pentane bis-boronates.Nature chemistry · 2024Article
- Enantioselective synthesis of chiral BCPs.Organic chemistry frontiers : an international journal of organic chemistry · 2024Review
- Light-enabled scalable synthesis of bicyclo[1.1.1]pentane halides and their functionalizations.Nature synthesis · 2024Article
- Recent advances in catalytic asymmetric synthesis.Frontiers in chemistry · 2024Review
- Selective P450Journal of the American Chemical Society · 2023Article
- Bicyclopentylation of Alcohols with Thianthrenium Reagents.Journal of the American Chemical Society · 2023Article
- 2-Oxabicyclo[2.1.1]hexanes as saturated bioisosteres of the ortho-substituted phenyl ring.Nature chemistry · 2023Article
- One-Pot Synthesis of Difluorobicyclo[1.1.1]pentanes from α-Allyldiazoacetates.Organic letters · 2023Article
- Review
- Synthesis of Sulfur-Substituted Bicyclo[1.1.1]pentanes by Iodo-Sulfenylation of [1.1.1]Propellane.Organic letters · 2022Article
Corrections and comments
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Authors and funding
5 authors at 3 institutions in 2 countries.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Bicyclo[1.1.1]pentanes (BCPs) are important motifs in contemporary drug design as linear spacer units that improve pharmacokinetic profiles. The synthesis of BCPs featuring adjacent stereocenters is highly challenging, but desirable due to the fundamental importance of 3D chemical space in medicinal chemistry. Current methods to access these high-value chiral molecules typically involve transformations of pre-formed BCPs, and can display limitations in substrate scope. Here we describe an approach to synthesize α-chiral BCPs involving the direct, asymmetric addition of simple aldehydes to [1.1.1]propellane, the predominant BCP precursor. This is achieved by combining a photocatalyst and an organocatalyst to generate a chiral α-iminyl radical cation intermediate, which installs a stereocenter simultaneously with ring-opening of [1.1.1]propellane. The reaction proceeds under mild conditions, displays broad scope, and provides an array of α-chiral BCPs in high yield and enantioselectivity. We also present a theoretical model for stereoinduction in this mode of photoredox organocatalysis.
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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.