ArticleAngewandte Chemie (International ed. in English)2019
Catalytic Enantioselective Synthesis of Allylic Boronates Bearing a Trisubstituted Alkenyl Fluoride and Related Derivatives.
Article in Angewandte Chemie (International ed. in English), 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 20 papers.
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Who cites it
20 citing papers in PubMed.
- Enantioselective synthesis of allylic boronates bearing a stereodefined (Organic chemistry frontiers : an international journal of organic chemistry · 2026Article
- Stereoselective Synthesis of Alkenyl Fluorides and Alkynes by Defluoro Coupling of Trifluoromethyl Arenes.Angewandte Chemie (International ed. in English) · 2025Article
- Applications of Olefin Metathesis in the Synthesis of Fluorinated Substrates and Design of Fluorinated Catalysts.Topics in current chemistry (Cham) · 2025Review
- Copper-Catalyzed Diastereoselective Defluoroborylation of Pentafluoroethyl Alkenes Using (pin)B-B(dan).Organic letters · 2025Article
- Hydrocyclization/Defluorination of CFAdvanced science (Weinheim, Baden-Wurttemberg, Germany) · 2025Article
- Article
- Cu-Bpin-mediated dimerization of 4,4-dichloro-2-butenoic acid derivatives enables the synthesis of densely functionalized cyclopropanes.Beilstein journal of organic chemistry · 2025Article
- Synthesis ofJournal of the American Chemical Society · 2024Article
- Synthetic Advantages of Defluorinative C-F Bond Functionalization.Angewandte Chemie (International ed. in English) · 2023Review
- Copper-Catalyzed Regio- and Enantioselective Hydroboration of Difluoroalkyl-Substituted Internal Alkenes.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2023Article
- Stereospecific Nickel-Catalyzed Cross-Electrophile Coupling Reaction of Alkyl Mesylates and Allylic Difluorides to Access Enantioenriched Vinyl Fluoride-Substituted Cyclopropanes.ACS catalysis · 2023Article
- Electrochemical Synthesis of gem-Difluoro- and γ-Fluoro-Allyl Boronates and Silanes.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Article
- Nickel-catalyzed enantioselective α-heteroarylation of ketonesChemical science · 2022Article
- Review
- Generation of Axially Chiral Fluoroallenes through a Copper-Catalyzed Enantioselective β-Fluoride Elimination.Journal of the American Chemical Society · 2021Article
- Organocatalytic Synthesis of α-Trifluoromethyl Allylboronic Acids by Enantioselective 1,2-Borotropic Migration.Journal of the American Chemical Society · 2020Article
- Sulfonate N-Heterocyclic Carbene-Copper Complexes: Uniquely Effective Catalysts for Enantioselective Synthesis of C-C, C-B, C-H, and C-Si Bonds.Angewandte Chemie (International ed. in English) · 2020Review
- Copper-Catalyzed Defluorinative Borylation and Silylation ofOrganic letters · 2020Article
- Beyond Carbon: Enantioselective and Enantiospecific Reactions with Catalytically Generated Boryl- and Silylcopper Intermediates.ACS central science · 2020Review
- Recent advances in Cu-catalyzed C(spBeilstein journal of organic chemistry · 2020Review
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9 authors.
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Abstract
The first catalytic method for diastereo- and enantioselective synthesis of allylic boronates bearing a Z-trisubstituted alkenyl fluoride is disclosed. Boryl substitution is performed with either a Z- or E-allyldifluoride and is catalyzed by bisphosphine/Cu complexes, affording products in up to 99 % yield with >98:2 Z/E selectivity and 99:1 enantiomeric ratio. A variety of subsequent modifications are feasible, and notable examples are diastereoselective additions to aldehydes/aldimines to access homoallylic alcohols/amines containing a fluorosubstituted stereogenic quaternary center.
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