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Organocatalytic Enantioselective Synthesis of Atropisomeric Aryl‐ p ‐Quinones: Platform Molecules for Diversity‐Oriented Synthesis of Biaryldiols
Author(s) -
Chen YeHui,
Li HengHui,
Zhang Xiao,
Xiang ShaoHua,
Li Shaoyu,
Tan Bin
Publication year - 2020
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202004671
Subject(s) - enantioselective synthesis , aryl , chemistry , molecule , chirality (physics) , quinone , axial chirality , stereochemistry , combinatorial chemistry , organocatalysis , catalysis , organic chemistry , physics , chiral symmetry breaking , symmetry breaking , alkyl , quantum mechanics , nambu–jona lasinio model
Presented here is a class of novel axially chiral aryl‐ p ‐quinones as platform molecules for the preparation of non‐ C 2 symmetric biaryldiols. Two sets of aryl‐ p ‐quinone frameworks were synthesized with remarkable enantiocontrol by means of chiral phosphoric acid catalyzed enantioselective arylation of p ‐quinones by central‐to‐axial chirality conversion. These aryl‐ p ‐quinones were then used to access a wide spectrum of highly functionalized non‐ C 2 symmetric biaryldiols with excellent retention of the enantiopurity.