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Asymmetric Reactions involving Lewis Base Catalyst Tethered Dearomatized Intermediates
Author(s) -
Xiao BenXian,
Gao XinYue,
Du Wei,
Chen YingChun
Publication year - 2019
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201803592
Subject(s) - electrophile , catalysis , chemistry , lewis acids and bases , aryl , organic chemistry , combinatorial chemistry , enantioselective synthesis , cycloaddition , organocatalysis , alkyl
Numerous protocols have been developed for the functionalization of aromatic substances. Among them, the strategy by which aromatic substrates are activated in situ to generate dearomatized intermediates is highly efficient but challenging, especially in the field of asymmetric catalysis. In this Concept article, the application of some well‐established chiral Lewis base catalysis, including primary/secondary amines and N‐heterocyclic carbenes, that can covalently form catalyst‐tethered dearomatized ortho / para ‐quinodimethane species with diverse heteroaryl and aryl carbonyl substrates is summarized in a number of asymmetric cycloaddition and addition reactions with diverse reagents generally having electrophilic properties. As a result, a variety of enantioenriched aromatic products with higher molecular complexity are constructed effectively through a rearomatization process.