Asymmetric Dearomative Cascade Multiple Functionalizations of Activated <i>N</i>-Alkylpyridinium and <i>N</i>-Alkylquinolinium Salts
Xue Song, Ru‐Jie Yan, Wei Du, Ying‐Chun Chen
Abstract
An enantioselective cascade reaction of N-alkylpyridinium and -quinolinium salts with o-hydroxybenzylideneacetones to access fused polyheterocycles through cross dienamine-mediated addition followed by trapping of the dearomatized enamine-type intermediates and aminal formation has been developed. A cascade assembly of N-benzyl-4-methylpyridinium salt and cyclic 2,4-dienones is further disclosed to give bridged frameworks via repetitive dearomatization and aromatization activation.
Topics & Concepts
ChemistryCascadeEnantioselective synthesisAminalAromatizationSalt (chemistry)EnamineStereochemistryMedicinal chemistryOrganic chemistryCombinatorial chemistryCatalysisChromatographyAsymmetric Synthesis and CatalysisCatalytic C–H Functionalization MethodsAdvanced Synthetic Organic Chemistry