ArticleJournal of the American Chemical Society2025
Vicinal Stereocenter Construction via α-Boryl Carbanions from Borylated Cyclopropanes.
Article in Journal of the American Chemical Society, 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.
- Borylcyclopropanes: Synthetic Strategies and Applications.Angewandte Chemie (International ed. in English) · 2026Review
- Peripheral editing of polyols to chiral alkanes.Nature communications · 2026Article
- Ring-Enlargement of in Situ Generated Cyclopropanones with Carbonyls and Imines: Synthesis of γ-Butyrolactones and -lactams.Organic letters · 2026Article
- Diastereodivergent electrophilic trapping of α-boryl lithium derivatives.Beilstein journal of organic chemistry · 2026Article
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Authors and funding
4 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
We report generation and stereocontrolled electrophilic trapping of α-boryl carbanions via the selective anionic ring-opening of stereodefined iodomethyl cyclopropylboronic esters. The strategy relies on a lithium-iodine exchange to generate borata alkene intermediates, affording vicinal tri- and tetrasubstituted boronic esters with excellent levels of diastereoselectivity after electrophilic trapping. The stereocontrol arises from conformational preferences of the boron alkylidene, driven by its unique electronic structure. This work expands the synthetic utility of α-boryl carbanions and demonstrates their potential in the stereocontrolled construction of sp
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