Stereoselective Synthesis of Atropisomeric Acridinium Salts by the Catalyst‐Controlled Cyclization of ortho ‐Quinone Methide Iminiums

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Abstract: Quinone methides are fundamental intermediates for a wide range of reactions in which catalyst stereocontrol is often achieved by hydrogen bonding. Herein, we describe the feasibility of an intramolecular Friedel–Crafts 6π electrocyclization through ortho‐quinone methide iminiums stereocontrolled by a contact ion pair. A disulfonimide catalyst activates racemic trichloroacetimidate substrates and imparts stereocontrol in the cyclization step, providing a new avenue for selective ortho‐quinone methide iminium functionalization. A highly stereospecific oxidation readily transforms the enantioenriched acridanes into rotationally restricted acridiniums. Upon ion exchange, the method selectively affords atropisomeric acridinium tetrafluoroborate salts in high yields and an enantioenrichment of up to 93: 7 e.r. We envision that ion‐pairing catalysis over ortho‐quinone methide iminiums enables the selective synthesis of a diversity of heterocycles and aniline derivatives with distinct stereogenic units.

Location: Deutsche Nationalbibliothek Frankfurt am Main

Extent: Online-Ressource

Language: Englisch

Bibliographic citation: Stereoselective Synthesis of Atropisomeric Acridinium Salts by the Catalyst‐Controlled Cyclization of ortho ‐Quinone Methide Iminiums ; day:25 ; month:02 ; year:2022 ; extent:1
Angewandte Chemie ; (25.02.2022) (gesamt 1)

Creator: Wu, Xingxing
Sparr, Christof

DOI: 10.1002/ange.202201424

URN: urn:nbn:de:101:1-2022022514151477645662

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

Last update: 15.08.2025, 7:25 AM CEST

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Wu, Xingxing
Sparr, Christof

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Enantioselective Catalytic (4+1)‐Cyclization of ortho ‐Hydroxy‐ para ‐Quinone Methides with Allenoates

Enantioselective Catalytic (4+1)‐Cyclization of ortho ‐Hydroxy‐ para ‐Quinone Methides with Allenoates

Enantioselective cycloaddition reactions of ortho-quinone methide imines

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Completing the Redox‐Series of Silicon Trisdioxolene: ortho ‐Quinone and Lewis Superacid Make a Powerful Redox Catalyst

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Mannich base-connected syntheses mediated by ortho-quinone methides

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Asymmetric Catalytic Transformations of Aza‐ ortho ‐ and Aza‐ para ‐Quinone Methides

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Intramolecular [4+2] Cycloaddition of ortho-Quinone Methides Generated In Situ

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Defining the Synthetic Scope of ortho ‐Quinone Methides by Quantifying their Electrophilicity

Defining the Synthetic Scope of ortho ‐Quinone Methides by Quantifying their Electrophilicity

Ortho ‐Quinone Methide Driven Synthesis of New O, N ‐ or N, N ‐Heterocycles

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On-Surface Cyclization of ortho-Dihalotetracenes to Four- and Six-Membered Rings

On-Surface Cyclization of ortho-Dihalotetracenes to Four- and Six-Membered Rings

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