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Stereoselective Synthesis of Atropisomeric Acridinium Salts by the Catalyst-Controlled Cyclization of ortho-Quinone Methide Iminiums
JournalArticle (Originalarbeit in einer wissenschaftlichen Zeitschrift)
 
ID 4649151
Author(s) Wu, Xingxing; Sparr, Christof
Author(s) at UniBasel Wu, Xingxing
Sparr, Christof
Year 2022
Title Stereoselective Synthesis of Atropisomeric Acridinium Salts by the Catalyst-Controlled Cyclization of ortho-Quinone Methide Iminiums
Journal Angewandte Chemie International Edition
Volume 61
Number 19
Pages / Article-Number e202201424
Mesh terms Catalysis; Cyclization; Indolequinones, chemistry; Salts
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.
Publisher Wiley
ISSN/ISBN 1433-7851 ; 1521-3773
edoc-URL https://edoc.unibas.ch/89848/
Full Text on edoc Available
Digital Object Identifier DOI 10.1002/anie.202201424
PubMed ID http://www.ncbi.nlm.nih.gov/pubmed/35167176
ISI-Number 000773867100001
Document type (ISI) Journal Article
 
   

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12/05/2024