Organocatalytic Enantioselective Synthesis of Atropisomeric Aryl‐p‐Quinones: Platform Molecules for Diversity‐Oriented Synthesis of Biaryldiols. Issue 28 (7th May 2020)

• Record Type: Journal Article
• Authors: Chen, Ye‐Hui; Li, Heng‐Hui; Zhang, Xiao; Xiang, Shao‐Hua; Li, Shaoyu; Tan, Bin
• Is Part Of: Angewandte Chemie international edition. Volume 59:Issue 28(2020)
• Page Start: 11374
• Page End: 11378
• Publication Date: 2020-05-07
• Subjects: atropisomerism -- biaryls -- chirality -- organocatalysis -- quinones; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.202004671
• Languages: English
• ISSNs: 1433-7851

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. Abstract : A class of atropisomeric aryl‐ p ‐quinones were efficiently assembled by means of chiral phosphoric acid catalyzed enantioselective arylation of p ‐quinones through a central‐to‐axial chirality transfer process. This novel axially chiral framework served as a platform for diversity‐oriented synthesis of a wide range of highly functionalized non‐ C 2 symmetric biaryldiols with preservation of the chirality.