Asymmetric synthesis of N–N axially chiral compounds <i>via</i> organocatalytic atroposelective <i>N</i>-acylation
Wei Lin, Qun Zhao, Yao Li, Ming Pan, Chen Yang, Guohui Yang, Xin Li
Abstract
-acylation reaction of quinazolinone type benzamides with cinnamic anhydrides for the direct catalytic synthesis of optically active atropisomeric quinazolinone derivatives. This reaction features mild conditions and a broad substrate scope and produces N-N axially chiral compounds with high yields and very good enantioselectivities. Besides, the synthetic utility of the protocol was proved by a large scale reaction, transformation of the product and the utilization of the product as an acylation kinetic resolution reagent. Moreover, DFT calculations provide convincing evidence for the interpretation of stereoselection.
Topics & Concepts
QuinazolinoneAcylationChemistryOptically activeCatalysisEnantioselective synthesisOrganocatalysisOrganic chemistryCombinatorial chemistryAxial and Atropisomeric Chirality SynthesisMolecular spectroscopy and chiralityChemical synthesis and alkaloids