ArticleNature communications2024
Facile access to bicyclo[2.1.1]hexanes by Lewis acid-catalyzed formal cycloaddition between silyl enol ethers and bicyclo[1.1.0]butanes.
Article in Nature communications, 2024. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 9 papers.
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Who cites it
9 citing papers in PubMed.
- Recent Progress in Coupling Reactions Involving the Novel Substrate of Bicyclo[1.1.0]butane (BCB).Topics in current chemistry (Cham) · 2026Review
- Catalytic asymmetric tandem Heck/Sonogashira reaction enabling access to versatile chiral bridged ring scaffolds.Nature communications · 2025Article
- Article
- Organocatalytic enantioselective [2π + 2σ] cycloaddition reactions of bicyclo[1.1.0]butanes with α,β-unsaturated aldehydes.Nature communications · 2025Article
- Ring expansion of bicyclo[1.1.0]butyl ketones to bicyclo[2.1.1]hexenes using ketone as both activating and reacting groups.Nature communications · 2025Article
- [2,3]-Sigmatropic rearrangement with [1.1.1]propellane.Nature communications · 2025Article
- Photoinduced cobaloxime catalysis enabled dehydrogenative C2-phosphinylation of bicyclo[1.1.0]butanes to access phosphorylated cyclobutenes.RSC advances · 2025Article
- Catalyst-Controlled Divergent Synthesis of Bicyclo[2.1.1]hexanes and Cyclobutenes: The Unique Effect of Au(I).JACS Au · 2025Article
- Facile access to bicyclo[2.1.1]hexanes by Lewis acid-catalyzed formal cycloaddition between silyl enol ethers and bicyclo[1.1.0]butanes.Nature communications · 2024Article
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Authors and funding
4 authors.
Funding
Abstract
Saturated three-dimensional carbocycles have gained increasing prominence in synthetic and medicinal chemistry. In particular, bicyclo[2.1.1]hexanes (BCHs) have been identified as the molecular replacement for benzenes. Here, we present facile access to a variety of BCHs via a stepwise two-electron formal (3 + 2) cycloaddition between silyl enol ethers and bicyclo[1.1.0]butanes (BCBs) under Lewis acid catalysis. The reaction features wide functional group tolerance for silyl enol ethers, allowing the efficient construction of two vicinal quaternary carbon centers and a silyl-protected tertiary alcohol unit in a streamlined fashion. Interestingly, the reaction with conjugated silyl dienol ethers can provide access to bicyclo[4.1.1]octanes (BCOs) equipped with silyl enol ethers that facilitate further transformation. The utilities of this methodology are demonstrated by the late-stage modification of natural products, transformations of tertiary alcohol units on bicyclo[2.1.1]hexane frameworks, and derivatization of silyl enol ethers on bicyclo[4.1.1]octanes, delivering functionalized bicycles that are traditionally inaccessible.
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