Organocatalytic Atroposelective Construction of Axially Chiral <i>N</i>-Aryl Benzimidazoles Involving Carbon–Carbon Bond Cleavage
Ningning Man, Zhenbang Lou, Yuming Li, Haijun Yang, Yufen Zhao, Hua Fu
Abstract
Axially chiral compounds widely occur in natural products, biologically active molecules, ligands, and catalysts, and their efficient and enantioselective synthesis is highly desirable. Herein, we report a novel method for the atroposelective construction of axially chiral N-aryl benzimidazoles with chiral phosphoric acid as the organocatalyst via reaction of N1-(aryl)benzene-1,2-diamines with multicarbonyl compounds. The present method provided the target products in high yields (up to 89%) with excellent enantioselectivity (up to 98% ee).
Topics & Concepts
ChemistryArylEnantioselective synthesisPhosphoric acidAxial symmetryCatalysisCombinatorial chemistryAxial chiralityMoleculeBenzeneOrganic chemistryStructural engineeringAlkylEngineeringAxial and Atropisomeric Chirality SynthesisMolecular spectroscopy and chiralitySphingolipid Metabolism and Signaling