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

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Abstract: Enantiomerically enriched crown ethers (CE) exhibit strong asymmetric induction in phase transfer catalysis, supramolecular catalysis and molecular recognition processes. Traditional methods have often been used to access these valuable compounds, which limit their diversity and consequently their applicability. Herein, a practical catalytic method is described for the gram scale synthesis of a class of chiral CEs (aza‐crown ethers; ACEs) using Rh‐catalyzed hydroamination of bis (allenes) with diamines. Using this approach, a wide range of chiral vinyl functionalized CEs with ring sizes ranging from 12 to 36 have been successfully prepared in high yields of up to 92 %, dr of up to >20: 1 and er of up to >99: 1. These vinyl substituted CEs allow for further diversification giving facile access to various CE derivatives as well as to their three‐dimensional analogues using ring‐closing metathesis. Some of these chiral CEs themselves display high potential for use in asymmetric catalysis.

Location: Deutsche Nationalbibliothek Frankfurt am Main

Extent: Online-Ressource

Language: Englisch

Bibliographic citation: Rhodium‐Catalyzed Asymmetric Macrocyclization towards Crown Ethers Using Hydroamination of Bis (allenes) ; day:28 ; month:02 ; year:2024 ; extent:12
Angewandte Chemie ; (28.02.2024) (gesamt 12)

Creator: Panahi, Farhad
Breit, Bernhard

DOI: 10.1002/ange.202317981

URN: urn:nbn:de:101:1-2024022814284583418315

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

Last update: 14.08.2025, 10:58 AM CEST

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Associated

Panahi, Farhad
Breit, Bernhard

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

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

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

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

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

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

Hochschulschrift

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

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

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

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

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

Rhodium-catalyzed addition of alcohols and N-hydroxy imides to allenes and alkynes

Rhodium-catalyzed addition of alcohols and N-hydroxy imides to allenes and alkynes

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

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