Strong Brønsted acid promoted asymmetric hydrogenation of isoquinolines and quinolines catalyzed by a Rh–thiourea chiral phosphine complex via anion binding

Abstract

Rhodium catalyzed asymmetric hydrogenation of both isoquinolines and quinolines provides a new method to synthesize chiral tetrahydroisoquinolines and tetrahydroquinolines. By introducing strong Brønsted acid HCl, anion binding between the substrate and the ligand was established to achieve high reactivity and high enantioselectivity (up to 99% conversion and 99% ee). An NMR study suggests an anion binding between the catalyst and the substrate. Deuterium labeling experiments reveal a plausible reaction pathway.