ArticleNature communications2024
Carbon-silicon-switch effect in enantioselective construction of silicon-stereogenic center from silacyclohexadienones.
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 4 papers.
What it found
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The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
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Who cites it
4 citing papers in PubMed.
- Chemically Interpretable Prediction Models for Silicon and Germanium Bond Dissociation Enthalpies.ACS omega · 2026Article
- Catalytic asymmetric construction of remote P or other heteroatom (Si/S) stereogenic axially chiral scaffolds.Chemical science · 2026Article
- Mechanistic Insights into the Coupling of Hydrosilanes and Alcohol-Amines for Hydrogen Production.ACS omega · 2025Article
- Applications of carbon-silicon bioisosterism in drug design and development.Future medicinal chemistry · 2025Article
Corrections and comments
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Authors and funding
6 authors.
Funding
Abstract
Carbon-silicon-switch strategy, replacing one specific carbon atom in organic molecules with a silicon, has garnered significant interest for developing new functional molecules. However, the influence of a reaction regarding its selectivity and reactivity by carbon-silicon-switch strategy has far less been investigated. Here we discover an unusual carbon-silicon-switch effect in the enantioselective construction of silicon-stereogenic center. It is found that there has been a significant change in the desymmetrization reaction of silacyclohexadienones using asymmetric conjugate addition or oxidative Heck reaction with aryl/alkyl nucleophiles when compared with their carbon analogues cyclohexadienones. Specifically, the carbon-silicon-switch leads to a reversal in enantioselectivity with arylzinc as the nucleophile by the same chiral catalyst, and results in totally different reactivity with arylboronic acid as the nucleophile. Control experiments and density functional theory (DFT) calculations have shown that the unusual carbon-silicon-switch effect comes from the unique stereoelectronic feature of silicon.
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Registered trials
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