Organocatalytic Enantioselective Synthesis of Atropisomeric Aryl‐<i>p</i>‐Quinones: Platform Molecules for Diversity‐Oriented Synthesis of Biaryldiols
Ye‐Hui Chen, Heng‐Hui Li, Xiǎo Zhang, Shao‐Hua Xiang, Shaoyu Li, Bin Tan
Abstract
Abstract 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.
Topics & Concepts
Enantioselective synthesisArylChemistryMoleculeQuinoneChirality (physics)Axial chiralityStereochemistryCombinatorial chemistryPhosphoric acidCatalysisOrganic chemistryPhysicsChiral symmetry breakingSymmetry breakingAlkylQuantum mechanicsNambu–Jona-Lasinio modelAxial and Atropisomeric Chirality SynthesisAlkaloids: synthesis and pharmacologyMolecular spectroscopy and chirality