Asymmetric Synthesis of Hydroquinazolines Bearing C4-Tetrasubstituted Stereocenters via Kinetic Resolution of α-Tertiary Amines
Qian Jiang, Tianren Qin, Xiaoyu Yang
Abstract
A novel protocol for asymmetric synthesis of hydroquinazolines bearing C4-tetrasubstituted stereocenters has been achieved through kinetic resolution of 2-amido α-tertiary benzylamines via chiral phosphoric acid catalyzed intramolecular dehydrative cyclizations. This method gave access to both α-tertiary benzylamines and hydroquinazolines with broad scope and high enantioselectivities. An intriguing restricted rotation of the C-N bond was observed for hydroquinazoline products bearing C4-tetrasubstituted stereocenters.
Topics & Concepts
StereocenterChemistryKinetic resolutionIntramolecular forceStereochemistryPhosphoric acidBearing (navigation)Combinatorial chemistryCatalysisEnantioselective synthesisOrganic chemistryGeographyCartographyAdvanced Synthetic Organic ChemistryAsymmetric Hydrogenation and CatalysisAsymmetric Synthesis and Catalysis