Organocatalytic Atroposelective Construction of Axially Chiral Compounds Containing Benzimidazole and Quinoline Rings
Linan Hou, Sheng Zhang, Ji Ma, Haiyu Wang, Tienan Jin, Masahiro Terada, Ming Bao
Abstract
An organocatalytic atroposelective strategy for the construction of axially chiral compounds containing benzimidazole and quinoline rings is described. The enantioselective heteroannulation reaction of 2-alkynylbenzimidazoles with ortho- aminophenylketones proceeded smoothly in the presence of chiral phosphoric acid to provide axially chiral heterobiaryls with good yields and enantioselectivities. This is the first example of the combination of benzimidazole and quinoline rings at the 2- and 3-positions, respectively, into axially chiral heterobiaryls by this new strategy.
Topics & Concepts
BenzimidazoleQuinolineChemistryAxial symmetryPhosphoric acidEnantioselective synthesisCombinatorial chemistryAxial chiralityQuinazolineCatalysisOrganic chemistryStructural engineeringEngineeringAxial and Atropisomeric Chirality SynthesisMolecular spectroscopy and chiralityPlant and Fungal Species Descriptions