Rhodium‐Catalyzed Cyclization of Terminal and Internal Allenols: An Atom Economic and Highly Stereoselective Access Towards Tetrahydropyrans

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Abstract: A comprehensive study of a diastereoselective Rh‐catalyzed cyclization of terminal and internal allenols is reported. The methodology allows the atom economic and highly syn‐selective access to synthetically important 2,4‐disubstituted and 2,4,6‐trisubstituted tetrahydropyrans (THP). Furthermore, its utility and versatility are demonstrated by a great functional‐group compatibility and the enantioselective total synthesis of (−)‐centrolobine.

Location: Deutsche Nationalbibliothek Frankfurt am Main

Extent: Online-Ressource

Language: Englisch

Bibliographic citation: Rhodium‐Catalyzed Cyclization of Terminal and Internal Allenols: An Atom Economic and Highly Stereoselective Access Towards Tetrahydropyrans ; volume:132 ; number:52 ; year:2020 ; pages:23691-23696 ; extent:6
Angewandte Chemie ; 132, Heft 52 (2020), 23691-23696 (gesamt 6)

Creator: Schmidt, Johannes P.
Breit, Bernhard

DOI: 10.1002/ange.202009166

URN: urn:nbn:de:101:1-2022052813040598699724

Rights: Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.

Last update: 15.08.2025, 7:36 AM CEST

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Rhodium‐Catalyzed Cyclization of Terminal and Internal Allenols: An Atom Economic and Highly Stereoselective Access Towards Tetrahydropyrans

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Ligand‐Mediated Regioselective Rhodium‐Catalyzed Benzotriazole–Allene Coupling: Mechanistic Exploration and Quantum Chemical Analysis

Rhodium‐Catalyzed Cyclization of Terminal and Internal Allenols: An Atom Economic and Highly Stereoselective Access Towards Tetrahydropyrans

Rhodium‐catalyzed cyclization of terminal and internal allenols: an atom economic and highly stereoselective access towards tetrahydropyrans

Rhodium‐Catalyzed Asymmetric Macrocyclization towards Crown Ethers Using Hydroamination of Bis (allenes)

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Rhodium-catalyzed intra- and intermolecular alkene hydroacylation : = Rhodium-katalisierte Intra- und Intermolecular Alken Hydroacylation

Rhodium‐catalyzed asymmetric macrocyclization towards crown ethers using hydroamination of Bis(allenes)

Hochschulschrift

Phosphaalkincyclooligomerisierung zum Aufbau von Phosphor-Kohlenstoff-Käfigverbindungen : eine Untersuchung über das [2+2]-Cycloadditionsverhalten von Phosphaalkinen mit ausgewählten Reaktionspartnern

Rhodium-catalyzed regioselective addition of thioacids to terminal allenes: enantioselective access to branched allylic thioesters

Rhodium-catalyzed dynamic kinetic resolution of racemic internal allenes towards chiral allylated triazoles and tetrazoles

Rhodium-catalyzed asymmetric intramolecular hydroarylation of allenes: access to functionalized benzocycles

Rhodium‐Catalyzed Enantioselective Intramolecular Hydroalkoxylation of Allenes and Application in the Total Synthesis of (R,R,R)‐ α ‐Tocopherol

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Rhodium‐Catalyzed Cyclization of Terminal and Internal Allenols: An Atom Economic and Highly Stereoselective Access Towards Tetrahydropyrans

Rhodium‐catalyzed cyclization of terminal and internal allenols: an atom economic and highly stereoselective access towards tetrahydropyrans

Rhodium‐Catalyzed Asymmetric Macrocyclization towards Crown Ethers Using Hydroamination of Bis (allenes)

Hochschulschrift

Rhodium-catalyzed intra- and intermolecular alkene hydroacylation : = Rhodium-katalisierte Intra- und Intermolecular Alken Hydroacylation

Rhodium‐catalyzed asymmetric macrocyclization towards crown ethers using hydroamination of Bis(allenes)

Hochschulschrift

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Rhodium-catalyzed regioselective addition of thioacids to terminal allenes: enantioselective access to branched allylic thioesters

Rhodium-catalyzed dynamic kinetic resolution of racemic internal allenes towards chiral allylated triazoles and tetrazoles

Rhodium-catalyzed asymmetric intramolecular hydroarylation of allenes: access to functionalized benzocycles

Rhodium‐Catalyzed Enantioselective Intramolecular Hydroalkoxylation of Allenes and Application in the Total Synthesis of (R,R,R)‐ α ‐Tocopherol

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Rhodium‐Catalyzed Cyclization of Terminal and Internal Allenols: An Atom Economic and Highly Stereoselective Access Towards Tetrahydropyrans

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Other Objects (12)

Rhodium‐Catalyzed Cyclization of Terminal and Internal Allenols: An Atom Economic and Highly Stereoselective Access Towards Tetrahydropyrans

Rhodium‐catalyzed cyclization of terminal and internal allenols: an atom economic and highly stereoselective access towards tetrahydropyrans

Rhodium‐Catalyzed Asymmetric Macrocyclization towards Crown Ethers Using Hydroamination of Bis (allenes)

Rhodium‐Catalyzed Asymmetric Macrocyclization towards Crown Ethers Using Hydroamination of Bis (allenes)

Rhodium-catalyzed intra- and intermolecular alkene hydroacylation : = Rhodium-katalisierte Intra- und Intermolecular Alken Hydroacylation

Rhodium‐catalyzed asymmetric macrocyclization towards crown ethers using hydroamination of Bis(allenes)

Phosphaalkincyclooligomerisierung zum Aufbau von Phosphor-Kohlenstoff-Käfigverbindungen : eine Untersuchung über das [2+2]-Cycloadditionsverhalten von Phosphaalkinen mit ausgewählten Reaktionspartnern

Rhodium-catalyzed regioselective addition of thioacids to terminal allenes: enantioselective access to branched allylic thioesters

Rhodium-catalyzed dynamic kinetic resolution of racemic internal allenes towards chiral allylated triazoles and tetrazoles

Rhodium-catalyzed asymmetric intramolecular hydroarylation of allenes: access to functionalized benzocycles

Rhodium‐Catalyzed Enantioselective Intramolecular Hydroalkoxylation of Allenes and Application in the Total Synthesis of (R,R,R)‐ α ‐Tocopherol

Ligand‐Mediated Regioselective Rhodium‐Catalyzed Benzotriazole–Allene Coupling: Mechanistic Exploration and Quantum Chemical Analysis

Rhodium‐Catalyzed Cyclization of Terminal and Internal Allenols: An Atom Economic and Highly Stereoselective Access Towards Tetrahydropyrans

Rhodium‐catalyzed cyclization of terminal and internal allenols: an atom economic and highly stereoselective access towards tetrahydropyrans

Rhodium‐Catalyzed Asymmetric Macrocyclization towards Crown Ethers Using Hydroamination of Bis (allenes)

Rhodium‐Catalyzed Asymmetric Macrocyclization towards Crown Ethers Using Hydroamination of Bis (allenes)

Rhodium-catalyzed intra- and intermolecular alkene hydroacylation : = Rhodium-katalisierte Intra- und Intermolecular Alken Hydroacylation

Rhodium‐catalyzed asymmetric macrocyclization towards crown ethers using hydroamination of Bis(allenes)

Phosphaalkincyclooligomerisierung zum Aufbau von Phosphor-Kohlenstoff-Käfigverbindungen : eine Untersuchung über das [2+2]-Cycloadditionsverhalten von Phosphaalkinen mit ausgewählten Reaktionspartnern

Rhodium-catalyzed regioselective addition of thioacids to terminal allenes: enantioselective access to branched allylic thioesters

Rhodium-catalyzed dynamic kinetic resolution of racemic internal allenes towards chiral allylated triazoles and tetrazoles

Rhodium-catalyzed asymmetric intramolecular hydroarylation of allenes: access to functionalized benzocycles

Rhodium‐Catalyzed Enantioselective Intramolecular Hydroalkoxylation of Allenes and Application in the Total Synthesis of (R,R,R)‐ α ‐Tocopherol

Ligand‐Mediated Regioselective Rhodium‐Catalyzed Benzotriazole–Allene Coupling: Mechanistic Exploration and Quantum Chemical Analysis

Rhodium‐Catalyzed Cyclization of Terminal and Internal Allenols: An Atom Economic and Highly Stereoselective Access Towards Tetrahydropyrans

Rhodium‐catalyzed cyclization of terminal and internal allenols: an atom economic and highly stereoselective access towards tetrahydropyrans

Rhodium‐Catalyzed Asymmetric Macrocyclization towards Crown Ethers Using Hydroamination of Bis (allenes)

Rhodium‐Catalyzed Asymmetric Macrocyclization towards Crown Ethers Using Hydroamination of Bis (allenes)

Rhodium-catalyzed intra- and intermolecular alkene hydroacylation : = Rhodium-katalisierte Intra- und Intermolecular Alken Hydroacylation

Rhodium‐catalyzed asymmetric macrocyclization towards crown ethers using hydroamination of Bis(allenes)

Phosphaalkincyclooligomerisierung zum Aufbau von Phosphor-Kohlenstoff-Käfigverbindungen : eine Untersuchung über das [2+2]-Cycloadditionsverhalten von Phosphaalkinen mit ausgewählten Reaktionspartnern

Rhodium-catalyzed regioselective addition of thioacids to terminal allenes: enantioselective access to branched allylic thioesters

Rhodium-catalyzed dynamic kinetic resolution of racemic internal allenes towards chiral allylated triazoles and tetrazoles

Rhodium-catalyzed asymmetric intramolecular hydroarylation of allenes: access to functionalized benzocycles

Rhodium‐Catalyzed Enantioselective Intramolecular Hydroalkoxylation of Allenes and Application in the Total Synthesis of (R,R,R)‐ α ‐Tocopherol

Ligand‐Mediated Regioselective Rhodium‐Catalyzed Benzotriazole–Allene Coupling: Mechanistic Exploration and Quantum Chemical Analysis

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