Bridged Biaryl Atropisomers by Organocatalyzed Kinetic Asymmetric Alcoholysis
Zhikang Wei, Yi Zhao, Tianyi Wang, Jiaomeng Li, Wei Yuan, Liwen Wei, Xing Yang
Abstract
We disclose herein an asymmetric synthesis of axially chiral oxazepine-containing bridged biaryls via CPA-catalyzed kinetic asymmetric alcoholysis. Control experiments showed that this CPA-catalyzed alcoholysis was reversible, and lowering the reaction temperature could almost suppress the reversible reaction, thus providing a series of axially chiral oxazepine-containing bridged biaryl compounds in good to excellent enantioselectivities. The gram-scale reactions and facile derivatizations of the enantioenriched products demonstrate the practical utility of this reaction.
Topics & Concepts
AtropisomerChemistryCatalysisAxial symmetryEnantioselective synthesisCombinatorial chemistryKinetic resolutionOrganocatalysisReaction conditionsKinetic energyOrganic chemistryEngineeringQuantum mechanicsPhysicsStructural engineeringAxial and Atropisomeric Chirality SynthesisMolecular spectroscopy and chiralityAsymmetric Synthesis and Catalysis