Enantio‐ and Diastereoselective Suzuki–Miyaura Coupling with Racemic Bicycles
Abstract: Herein, we describe a rhodium‐catalyzed enantio‐ and diastereoselective Suzuki–Miyaura cross‐coupling between racemic fused bicyclic allylic chlorides and boronic acids. The highly stereoselective transformation allows for the coupling of aryl, heteroaryl, and alkenyl boronic acids and gives access to functionalized bicyclic cyclopentenes, which can be converted into other five‐membered‐ring scaffolds with up to five contiguous stereocenters. Preliminary mechanistic studies suggest that these reactions occur with overall retention of the relative stereochemistry and are enantioconvergent for pseudo‐symmetric allylic chloride starting materials. In addition, a bicyclic allylic chloride starting material without pseudo‐symmetry undergoes a highly enantioselective regiodivergent reaction.
- Location
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Deutsche Nationalbibliothek Frankfurt am Main
- Extent
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Online-Ressource
- Language
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Englisch
- Bibliographic citation
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Enantio‐ and Diastereoselective Suzuki–Miyaura Coupling with Racemic Bicycles ; volume:58 ; number:35 ; year:2019 ; pages:12128-12132 ; extent:5
Angewandte Chemie / International edition. International edition ; 58, Heft 35 (2019), 12128-12132 (gesamt 5)
- Creator
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Goetzke, F. Wieland
Mortimore, Mike
Fletcher, Stephen P.
- DOI
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10.1002/anie.201906478
- URN
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urn:nbn:de:101:1-2022070807451975406841
- Rights
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Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
- Last update
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15.08.2025, 7:32 AM CEST
Data provider
Deutsche Nationalbibliothek. If you have any questions about the object, please contact the data provider.
Associated
- Goetzke, F. Wieland
- Mortimore, Mike
- Fletcher, Stephen P.
Other Objects (12)
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Suzuki–Miyaura Coupling Using Polymer-Stabilized Pd Nanoparticles
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Peptide stapling by late-stage Suzuki–Miyaura cross-coupling
Cyclization by Intramolecular Suzuki‐Miyaura Cross‐Coupling–A Review
Direct Suzuki-Miyaura Coupling of Phenol Derivatives via Mutual Activation
Suzuki-Miyaura Coupling Reaction Using Palladium Nanoparticles Immobilized on SPB
Suzuki-Miyaura Coupling in Water Using an NHC-Pd Polymer
Enantio‐ and Diastereoselective Suzuki–Miyaura Coupling with Racemic Bicycles
Suzuki-Miyaura Cross-Coupling of Trifluoroboratohomoenolates
Nickel-Catalyzed Suzuki–Miyaura Cross-Coupling
The Suzuki-Miyaura Coupling with PdPeptide
Suzuki–Miyaura Coupling Using Polymer-Stabilized Pd Nanoparticles
Suzuki–Miyaura Coupling with Main-Chain Organometallic Polymer
Suzuki-Miyaura Coupling through C-CN Bond Cleavage
Peptide stapling by late-stage Suzuki–Miyaura cross-coupling
Cyclization by Intramolecular Suzuki‐Miyaura Cross‐Coupling–A Review
Direct Suzuki-Miyaura Coupling of Phenol Derivatives via Mutual Activation
Suzuki-Miyaura Coupling Reaction Using Palladium Nanoparticles Immobilized on SPB
Suzuki-Miyaura Coupling in Water Using an NHC-Pd Polymer
Enantio‐ and Diastereoselective Suzuki–Miyaura Coupling with Racemic Bicycles
Suzuki-Miyaura Cross-Coupling of Trifluoroboratohomoenolates
Nickel-Catalyzed Suzuki–Miyaura Cross-Coupling
The Suzuki-Miyaura Coupling with PdPeptide
Suzuki–Miyaura Coupling Using Polymer-Stabilized Pd Nanoparticles
Suzuki–Miyaura Coupling with Main-Chain Organometallic Polymer
Suzuki-Miyaura Coupling through C-CN Bond Cleavage
Peptide stapling by late-stage Suzuki–Miyaura cross-coupling
Cyclization by Intramolecular Suzuki‐Miyaura Cross‐Coupling–A Review
Direct Suzuki-Miyaura Coupling of Phenol Derivatives via Mutual Activation
Suzuki-Miyaura Coupling Reaction Using Palladium Nanoparticles Immobilized on SPB