Palladium-catalyzed stereoselective domino arylation–acylation: an entry to chiral tetrahydrofluorenone scaffolds

Dunås, Petter; Paterson, Andrew J.; Kociok‐Köhn, Gabriele; Rahm, Martin; Lewis, Simon E.; Kann, Nina

doi:10.1039/d1cc02160e

Chem. Commun.

2021

DOI: 10.1039/d1cc02160e

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Palladium-catalyzed stereoselective domino arylation–acylation: an entry to chiral tetrahydrofluorenone scaffolds

Petter Dunås

Andrew J. Paterson

Gabriele Kociok‐Köhn

et al.

Abstract: A palladium-catalyzed domino arylation-cyclization of biocatalytically derived cyclic 1,3-dienes is demonstrated. The reaction introduces a high degree of structural complexity in a single step, giving access to tricyclic tetrahydrofluorenones with...

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Cited by 3 publications

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Palladium‐Catalyzed Aminoalkylative Cyclization Enables Modular Synthesis of Exocyclic 1,3‐Dienes

Zou,

Zhao,

Huang

2023

Angewandte Chemie

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A novel and efficient palladium‐catalyzed regioselective and stereodivergent ring‐closing reaction of aminoenynes with aldehydes and boronic acids or hydrosilane is developed. This three‐component reaction allows for the modular synthesis of a series of exocyclic 1,3‐dienes bearing 5‐ to 8‐membered saturated N‐heterocycles. The reactions utilize a simple Pd‐catalyst and work with broad range of aminoenynes, aldehydes and organometallic reagents under mild reaction conditions. The products represent useful intermediates for chemical synthesis due to the versatility of the conjugated diene. Preliminary mechanistic details of the method are also revealed.

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Palladium‐Catalyzed Aminoalkylative Cyclization Enables Modular Synthesis of Exocyclic 1,3‐Dienes

Zou,

Zhao,

Huang

2023

Angewandte Chemie

View full text Add to dashboard Cite

show abstract

Palladium‐Catalyzed Aminoalkylative Cyclization Enables Modular Synthesis of Exocyclic 1,3‐Dienes

Zou,

Zhao,

Huang

2023

Angew Chem Int Ed

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Interrupted Corey–Chaykovsky Reaction of Tethered Bis-Enones to Access 2,3-Epoxy-hexahydrofluoren-9-ones

Maurya,

Ramasastry

2024

Org. Lett.

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The Corey−Chaykovsky reaction is usually employed to synthesize cyclopropanes from activated olefins. We intercepted the intermediates prevailing during this transformation and diverted the process for the creation of intricate molecular motifs. We describe an unusual skeletal remodelling of tethered bis-enones to 2,3-epoxy-hexahydrofluoren-9-ones via an "interrupted Corey−Chaykovsky reaction". The strategy rationally merges the nucleophilic features of sulfur ylides with electronically biased olefins to achieve the regio-and stereoselective synthesis of several new classes of hydrofluorenones. We have demonstrated the synthetic utility of the products in accessing several highly functionalized molecules.

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Palladium-catalyzed stereoselective domino arylation–acylation: an entry to chiral tetrahydrofluorenone scaffolds

Abstract: A palladium-catalyzed domino arylation-cyclization of biocatalytically derived cyclic 1,3-dienes is demonstrated. The reaction introduces a high degree of structural complexity in a single step, giving access to tricyclic tetrahydrofluorenones with...

Cited by 3 publications

References 40 publications

Palladium‐Catalyzed Aminoalkylative Cyclization Enables Modular Synthesis of Exocyclic 1,3‐Dienes

Palladium‐Catalyzed Aminoalkylative Cyclization Enables Modular Synthesis of Exocyclic 1,3‐Dienes

Palladium‐Catalyzed Aminoalkylative Cyclization Enables Modular Synthesis of Exocyclic 1,3‐Dienes

Interrupted Corey–Chaykovsky Reaction of Tethered Bis-Enones to Access 2,3-Epoxy-hexahydrofluoren-9-ones

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