ArticleChemical science2025
Strain-release enables access to carbonyl conjugated allylic diborons and alkenyl boronates having multiple contiguous stereocenters in a one-pot process.
Article in Chemical science, 2025. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 4 papers.
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Who cites it
4 citing papers in PubMed.
- (Poly)Borylated Species as Modern Reactive Groups toward Unusual Synthetic Applications.Angewandte Chemie (International ed. in English) · 2026Review
- Strain-Release Induced 1,2-Metallate Rearrangement of Geminal Diborons: Multicomponent 1,5-Difunctionalization via Ring-Opening Coupling.Angewandte Chemie (International ed. in English) · 2026Article
- Palladium-Catalyzed Gem-Diborylalkylation of Silyl Enol Ethers and N-Vinylacetamide via Diboryl Carbon-Centered Radicals.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2025Article
- Merging Ketyl Radical Chemistry and Allylboration via Strain Release: One-Pot Multicomponent Access to Sterically Congested Ketone-Functionalized Organoborons.Organic letters · 2025Article
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Authors and funding
6 authors.
Funding
Abstract
Allylic diboronates are highly valuable reagents in organic synthesis. Existing methods predominantly yield alkyl-substituted allylic diboronates, while the incorporation of electrophilic carbonyl groups conjugated to these allylic systems remains unknown. We present a strain-release promoted cycloaddition-based strategy that enabled access to unprecedented carbonyl conjugated secondary allylic diborons. This mild base-free method also facilitated a one-pot multicomponent cycloaddition-allylboration sequence for a highly diastereoselective installation of contiguous quaternary, tertiary and secondary carbon centers on a scaffold featuring valuable β-hydroxy ester, β-vinyl ester and vinyl boronate motifs. The synthetic utility of these densely functionalized products was demonstrated through their transformation into other rare and sterically congested alkenylborons such as borylated spiro-fused β-lactones and bicyclic γ-butyrolactones. Detailed
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Registered trials
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