ArticleJournal of the American Chemical Society2010
Enantioselective synthesis of allylboronates bearing a tertiary or quaternary B-substituted stereogenic carbon by NHC-Cu-catalyzed substitution reactions.
Article in Journal of the American Chemical Society, 2010. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 48 papers.
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Who cites it
48 citing papers in PubMed.
- Enantioselective synthesis of allylic boronates bearing a stereodefined (Organic chemistry frontiers : an international journal of organic chemistry · 2026Article
- 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
- Enantioselective synthesis of γ-chiral amides via copper-catalyzed reductive relay hydroaminocarbonylation.Nature communications · 2024Article
- Switching Selectivity in Borylative Allyl-Allyl Cross-Coupling through Synergistic Catalysis.Journal of the American Chemical Society · 2024Article
- Wingtip-Flexible N-Heterocyclic Carbenes: Unsymmetrical Connection between IMes and IPr.Angewandte Chemie (International ed. in English) · 2024Article
- A General Strategy for the Asymmetric Preparation of α-Stereogenic Allyl Silanes, Germanes, and Boronate Esters via Dual Copper Hydride- and Palladium-Catalysis.Angewandte Chemie (International ed. in English) · 2022Article
- Recent Advances in Catalysis Involving Bidentate N-Heterocyclic Carbene Ligands.Molecules (Basel, Switzerland) · 2021Review
- Enantioselective synthesis of tertiary boronic esters through catalytic asymmetric reversed hydroboration.Nature communications · 2021Article
- 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
- Beyond Carbon: Enantioselective and Enantiospecific Reactions with Catalytically Generated Boryl- and Silylcopper Intermediates.ACS central science · 2020Review
- Stereospecific Asymmetric Synthesis of Tertiary Allylic Alcohol Derivatives by Catalytic [2,3]-Meisenheimer Rearrangements.Angewandte Chemie (International ed. in English) · 2020Article
- Recent advances in Cu-catalyzed C(spBeilstein journal of organic chemistry · 2020Review
- Catalytic Enantioselective Synthesis of Allylic Boronates Bearing a Trisubstituted Alkenyl Fluoride and Related Derivatives.Angewandte Chemie (International ed. in English) · 2019Article
- Nickel-Catalyzed Arylboration of Alkenylarenes: Synthesis of Boron-Substituted Quaternary Carbons and Regiodivergent Reactions.Angewandte Chemie (International ed. in English) · 2019Article
- Facile access to functionalized chiral secondary benzylic boronic estersChemical science · 2019Article
- Enantioselective Construction of Tertiary Boronic Esters by Conjunctive Cross-Coupling.Angewandte Chemie (International ed. in English) · 2018Article
- Rhodium-catalyzed asymmetric hydroboration of γ,δ-unsaturated amide derivatives: δ-borylated amides.Chemical communications (Cambridge, England) · 2018Article
- A Simple Procedure for the Synthesis ofAdvanced synthesis & catalysis · 2018Article
- Mechanism-based enhancement of scope and enantioselectivity for reactions involving a copper-substituted stereogenic carbon centre.Nature chemistry · 2018Article
- Practical, efficient, and broadly applicable synthesis of readily differentiable vicinal diboronate compounds by catalytic three-component reactions.Tetrahedron · 2017Article
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Abstract
Allylic substitutions that afford alpha-substituted allylboronates bearing B-substituted tertiary or quaternary carbon stereogenic centers are presented. C-B bond-forming reactions, catalyzed by chiral bidentate Cu-NHC complexes, are performed in the presence of commercially available bis(pinacolato)diboron. Transformations proceed in high yield (up to >98%) and site selectivity (>98% S(N)2'), and in up to >99:1 enantiomer ratio. Trans- or cis-disubstituted alkenes can be used; alkyl- (linear as well as branched) and aryl-trisubstituted allylic carbonates serve as effective substrates. Allylboronates that bear a quaternary carbon center are air-stable and can be easily purified by silica gel chromatography; in contrast, secondary allylboronates cannot be purified in the same manner and are significantly less stable. Oxidation of the enantiomerically enriched products furnishes secondary or tertiary allylic alcohols, valuable small molecules that cannot be easily obtained in high enantiomeric purity by alternative synthesis or kinetic resolution approaches.
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