ArticleSynlett : accounts and rapid communications in synthetic organic chemistry2023
Development of Enantioselective Lithium-Isothiourea-Boronate-Catalyzed Matteson Homologations.
Article in Synlett : accounts and rapid communications in synthetic organic chemistry, 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 5 papers.
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Who cites it
5 citing papers in PubMed.
- Highly stereoselective synthesis of complex moleculesRSC advances · 2026Article
- Vicinal Stereocenter Construction via α-Boryl Carbanions from Borylated Cyclopropanes.Journal of the American Chemical Society · 2025Article
- Syntheses of Marine Natural Products via Matteson Homologations and Related Processes.Marine drugs · 2025Review
- Iterative Catalyst-Controlled Diastereoselective Matteson Homologations Enable the Selective Synthesis of Benzestrol Isomers.Journal of the American Chemical Society · 2024Article
- Enantioselective Potassium-Catalyzed Wittig Olefinations.Journal of the American Chemical Society · 2024Article
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Authors and funding
3 authors.
Funding
Abstract
Our group's discovery of lithium-isothiourea-boronate-catalyzed Matteson homologations is chronicled. Chiral thiourea dual-hydrogen bond donors were initially found to promote enantioselective dichloromethyl boronate rearrangements, albeit with poor reproducibility. Systematic investigations of the fate of the thiourea led to the discovery that lithium-isothiourea-boronate derivatives were being generated in situ as highly enantioselective catalytically active species. The optimal lithium-isothiourea-boronate catalyst displays significant generality in the rearrangement of primary alkyl migrating groups, affording synthetically valuable α-chloro boronic ester products with consistently high enantioselectivities. The catalyst is proposed to act as a structurally rigid chiral framework that precisely positions two lithium cations to enable a dual-lithium-mediated chloride abstraction.
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Registered trials
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