Asymmetric Synthesis of Quinoline-Naphthalene Atropisomers by Central-to-Axial Chirality Conversion
Shaojie Wang, Zhe Wang, Yue Tang, Jie Chen, Ling Zhou
Abstract
Asymmetric synthesis of quinoline-naphthalene atropisomers with fully blocked ortho positions has been developed by a two-step strategy, which contains a chiral phosphoric acid-catalyzed Povarov reaction and a DDQ oxidation reaction. This method provides facile access to diverse functionalized quinoline-naphthalene atropisomers with one or two chiral axes in excellent yields (≤98%) and excellent enantioselectivities (≤99% ee).
Topics & Concepts
AtropisomerQuinolineChemistryNaphthaleneAxial chiralityChirality (physics)CatalysisPhosphoric acidCombinatorial chemistryOrganic chemistryEnantioselective synthesisPhysicsNambu–Jona-Lasinio modelQuantum mechanicsQuarkChiral symmetry breakingAxial and Atropisomeric Chirality SynthesisMolecular spectroscopy and chiralitySynthesis and Properties of Aromatic Compounds