ArticleOrganic letters2013
Chiral Brønsted acid catalyzed enantioselective synthesis of anti-homopropargyl alcohols via kinetic resolution-aldehyde allenylboration using racemic allenylboronates.
Article in Organic letters, 2013. The graph could read no effect estimate from its abstract, so it casts no vote on the map. An erratum has been issued. Cited by 9 papers.
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Who cites it
9 citing papers in PubMed.
- Stereo- and Enantioselective Syntheses of (Organic letters · 2025Article
- NHC-Au-Catalyzed Isomerization of Propargylic B(MIDA)s to Allenes and Double Isomerization of Alkynes to 1,3-Dienes.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2024Article
- Photoredox cobalt-catalyzed regio-, diastereo- and enantioselective propargylation of aldehydes via propargyl radicals.Nature communications · 2023Article
- Unusual Enantiodivergence in Chiral Brønsted Acid-Catalyzed Asymmetric Allylation with β-Alkenyl Allylic Boronates.Angewandte Chemie (International ed. in English) · 2022Article
- Catalytic asymmetric transformations of racemic α-borylmethyl-(Chemical science · 2021Article
- Copper-catalyzed synthesis of allenylboronic acids. Access to sterically encumbered homopropargylic alcohols and amines by propargylboration.Chemical science · 2018Article
- Function-Oriented Studies Targeting Pectenotoxin 2: Synthesis of the GH-Ring System and a Structurally Simplified Macrolactone.Organic letters · 2017Article
- Chiral Brønsted Acid Catalyzed Kinetic Resolutions.Asian journal of organic chemistry · 2016Article
- Catalytic Borylative Opening of Propargyl Cyclopropane, Epoxide, Aziridine, and Oxetane Substrates: Ligand Controlled Synthesis of Allenyl Boronates and Alkenyl Diboronates.Angewandte Chemie (International ed. in English) · 2016Article
Corrections and comments
- Erratum issued
Authors and funding
3 authors.
Funding
Abstract
A chiral phosphoric acid catalyzed kinetic resolution/allenylboration of racemic allenylboronates with aldehydes is described. Allenylboration of aldehydes with 2.8 equiv of allenylboronate (±)-1 in the presence of 10 mol % of catalyst (R)-2 provided anti-homopropargyl alcohols 3 in 83-95% yield with 9:1 to 20:1 diastereoselectivity and 73-95% ee. The catalyst enables the kinetic resolution of the racemic allenylboronate (±)-1 to set the methyl stereocenter and biases the facial attack of the aldehyde to set the stereochemistry of the hydroxyl group in 3.
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