ArticleJournal of the American Chemical Society2012
Enantioselective synthesis of anti- and syn-homopropargyl alcohols via chiral Brønsted acid catalyzed asymmetric allenylboration reactions.
Article in Journal of the American Chemical Society, 2012. 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 16 papers.
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16 citing papers in PubMed, 89 citations in OpenAlex.
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- Electrochemical synthesis of allenyl silanes and allenyl boronic esters.Nature communications · 2025Article
- Stereo- and Enantioselective Syntheses of (Organic letters · 2025Article
- Highly Stereo- and Enantioselective Syntheses of δ-Alkyl-Substituted (Organic letters · 2025Article
- Axially chiral α-boryl-homoallenyl boronic esters as versatile toolbox for accessing centrally and axially chiral molecules.Nature communications · 2024Article
- Three-Component Approach to Densely Functionalized Trifluoromethyl Allenols by Asymmetric Organocatalysis.Journal of the American Chemical Society · 2023Article
- Iron-Catalyzed Borylation of Propargylic Acetates for the Synthesis of Multisubstituted Allenylboronates.Chemistry (Weinheim an der Bergstrasse, Germany) · 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
- Catalytic Enantioselective Carbonyl Propargylation Beyond Preformed Carbanions: Reductive Coupling and Hydrogen Auto-Transfer.ChemCatChem · 2019Article
- Copper-catalyzed synthesis of allenylboronic acids. Access to sterically encumbered homopropargylic alcohols and amines by propargylboration.Chemical science · 2018Article
- Catalytic, Enantioselective Synthesis of Allenyl Boronates.ACS catalysis · 2018Article
- Enantioselective Synthesis of Trisubstituted Allenyl-B(pin) Compounds by Phosphine-Cu-Catalyzed 1,3-Enyne Hydroboration. Insights Regarding Stereochemical Integrity of Cu-Allenyl Intermediates.Journal of the American Chemical Society · 2018Article
- 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
- Chiral Brønsted acid catalyzed enantioselective synthesis of anti-homopropargyl alcohols via kinetic resolution-aldehyde allenylboration using racemic allenylboronates.Organic letters · 2013Article
Corrections and comments
- Erratum issued
Authors and funding
2 authors at 1 institution in 1 country.
Funding
Abstract
Chiral Brønsted acid catalyzed asymmetric allenylboration reactions are described. Under optimized conditions, anti-homopropargyl alcohols 2 are obtained in high yields with excellent diastereo- and enantioselectivities from stereochemically matched aldehyde allenylboration reactions with (M)-1 catalyzed by the chiral phosphoric acid (S)-4. The syn-isomers 3 can also be obtained in good diastereoselectivities and excellent enantioselectivities from the mismatched allenylboration reactions of aromatic aldehydes using (M)-1 in the presence of the enantiomeric phosphoric acid (R)-4. The stereochemistry of the methyl group introduced into 2 and 3 is controlled by the chirality of the allenylboronate (M)-1, whereas the configuration of the new hydroxyl stereocenter is controlled by the enantioselectivity of the chiral phosphoric acid catalyst used in these reactions. The synthetic utility of this methodology was further demonstrated in highly diastereoselective syntheses of a variety of anti, anti-stereotriads, the direct synthesis of which has constituted a significant challenge using previous generations of aldol and crotylmetal reagents.
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Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.